How Rock Star CFO Tim Oakley Thinks About Hiring in the Finance Function

Tim Oakley, CFO of Appia and former CFO of iContact, is one of the Triangle’s best entrepreneurial executives.  With multiple exits and financings under his belt, and a commitment to servant leadership, we are fortunate to have him mentoring and guiding a generation of entrepreneurs (like me!) in the Triangle (the New Entrepreneurial Hub of the South).  Tim also formally does executive coaching at the Carolina Clinnic at UNC.

As Windsor Circle goes through the process of selecting and hiring a Director of Finance and Operations, Tim offered to spend some time with me thinking through strategy and candidates.

The first section is Tim’s “5 R’s of Finance.”  The following sections come from a scoring matrix that Tim shared with me.  I’ll use these subject areas to frame this post.  I’ll also offer suggested questions in italics to expound upon the areas in which one is qualifying a candidate.

The 5 Rs of Finance

This is a framework Tim shared with me for how to think at a high level about the G&A function.  I reframed it slightly to address how one hires in this function.

  1. Radar – Candidate has the systems, processes and management reporting that show issues early to be addressed and to capitalize on opportunities.
  2. Risk – Candidate can take calculated risks, identifying lower, expected and upside scenarios. The candidate should actively work towards “No Surprises” (especially on the downside!)
  3. Resources – Candidate needs to be able to allocate resources among multiple investment opportunities, and map them to present value of future cashflows (ie value), develop the people that work for her or him, and to support customers. Everything this function does should support “Selling Something to Somebody!”
  4. Reality – The candidate must collaborate with company leadership to define what the REAL story of the company is through monitoring metrics and relational and market information, and seasoning it with judgement and wisdom from her/his experience.
  5. Relationship – The candidate has to be able to built a trusted connection with the executive team and team members. This is especially true with the 15%-20% of the leadership team that is really driving the business (likely, but not always the CEO).

CFO Functional Knowledge – Day to Day

This section is from Tim’s scoring matrix, with elaboration based on our conversation.

Accounting, Financial Statements, and General Ledger (GL) 

This seems obvious but Tim pushed me here a bit.  There’s a difference between financial planning and modelling, and the act of closing the books on a routine basis.  Part of this is knowing how to handle accounting complexities in a subscription revenue business (such as deferred revenue schedules).  Another part of this is testing for the discipline to logically order a complex set of tactical requirements and keeping those trains moving on time.  

Tim shared that at iContact, he outsourced the bookkeeping function for quite a long time to a contract accountant.

Questions to ask during an interview:

  • Describe your experience closing the books and presenting financial statements to investors.
  • During the last audit, what did you find to be the most frustrating about the process?  What did you do to manage through it?
  • Imagine you’ve earned the job at Windsor Circle as Director of Finance and Operations.  Take 5 minutes to whiteboard your monthly, quarterly and annual responsibilities and then walk me through how you will manage it.

Payroll and Accounts Payable (AP)

Here, Tim was coaching me to think about the outflow of cash in one’s organization.  Getting everyone paid on time, and knowing how to manage vendors and contractors (and their payment terms) are critical skillsets, particularly during the early trajectory of a company given how crucial every dollar is.

Questions to ask during an interview:

  • Describe an instance where payroll was mishandled and what you did to overcome the error.
  • What is your philosophy on payment terms and how to pay vendors?
  • In the past, when faced with a cash shortfall, how did you manage AP to get the desired result?  What was the desired result?
  • What payroll systems do you have direct experience with?  If you earn the job here, what would you change about our current payroll system?

Accounts Receivable (AR)

Clearly, this is the inbound cash function.  In most businesses, these are payments from customers, but can also include payments from partners in the form of revenue sharing, commissions, etc.  As we scale from hundreds of clients to thousands of clients, with varying contract terms, and potentially across various products with different product and service profiles, this can get complex.  Tim wanted me to be sure I understood how someone in this function can keep a tight rein on the very source of life…  one’s inbound cash flow!

Questions to ask during an interview:

  • Describe the system you have used in the past to manage your client ledger.
  • How have you handled collections.
  • What critical measures do you use in this function? How will you know that you are collecting cash well?  (Days Sales Outstanding, or DSO, is key metric that should pop up in the answer).

Customer Resource Management (CRM) and IT Systems

I’m actually combining two sections here from Tim’s scoring matrix.  What (I think) I learned was that Tim was wanting to dig into a candidate’s ability to run the technology that runs the function.  CRM systems like or NetSuite allow one to keep all recorded interactions in a single place.  (At Windsor Circle, we strive to a corporate value of “Single Source of Truth” in our CRM and actively work to get everyone communicating through a single platform).

As he worked me through the IT systems component, he seemed very focused on the interface between the payment systems and billing technologies (at iContact, it was built into the customer facing app and required a pretty light implementation of QuickBooks to manage…  in other companies, the contracts and billing process are paper driven and may involve much higher degrees of complexity in the IT systems).

Questions to ask during an interview:

  • What CRM systems have you used in the past?
  • What complexities have you witnessed in the interactions between the CRM systems and the billing technology that you used in your prior roles?
  • Let’s say you won the position here, and had to completely revamp our CRM and billing systems…  whiteboard a plan for how you would tackle this and walk me through it.


An audit will be handled by an outside firm, so this line of questioning has more to do with how to manage an audit or review process.

  • Have you led an audit before?
  • What criteria is most important to you in selecting an audit firm?
  • What support systems and resources are required for a proficient audit?


Certified Public Accountant (CPA)

This is kind of a yes or no question.  Either the candidate has a CPA or not.  The knowledge you’re looking for here is an authoritative level of expertise with regards to Generally Accepted Accounting Practice (GAAP).  This, too, is a skillset that can be contracted in, but having someone inside your firm with a CPA provides for a level of efficiency, not just in audits, but in the general running of the finance function.

Planning and Analysis

A key indicator of expertise in this area is deep financial modeling capabilities.  In our selection process, we put one of our candidates under NDA and had her/him dig deep into our existing model with recommendations and analysis.  If the prior functional areas have to do with the tactical aspects of running the business, this subject area has to do with the strategy of running a business. One must quickly be able to model various scenarios, answer what-if statements, and think about future metrics assuming various aspects of the model come into being (or don’t!).

Questions to ask during an interview:

  • I’m going to have you sign an NDA, and then provide you with our financial model.  I’d like you to hit hard and pull no punches in preparing the 5 top things you’d modify about our business and our financial model.
  • In your opinion, what are the hardest parts of the financial model to get right?
  • Whiteboard the major aspects of your financial model and talk me through interdependencies.

Mergers and Acquisitions (M&A), Fundraising & Capital Markets

Deep expertise here is usually a CFO-level function.  Managing the complexities of due diligence and deal terms, as well as bringing the implied trust and connections of one’s personal network, are core aspects of this functional area.  If you’re hiring for a manager or director, exposure to these skillsets would be a plus, but perhaps not a requirement.  If you’re hiring for a CFO, they are a must.

Questions to ask during an interview:

  • Have you been through an acquisition?  Please describe the scenario and your role in it.
  • Describe your experience with fundraising?
  • What are the merits of venture debt versus equity?  Educate me on the terms that I’m likely to encounter in the market?
  • Have you ever been on a team that did an IPO?  What was that like?  What did you do well?  What did you do poorly and how did you overcome that?

Business Acumen

When Tim hit this area, it became clear to me that he was borrowing from a fair amount of intuition from years of experience.  What he seemed to be looking for was a candidate’s ability to rise above the noise of the function and sense what was happening in the business and to be an active participant in the prediction of what would happen next.  This also has to do with savviness…  sensing what’s happening in the team, in the market, and in the ecosystem.  I perceived here too that deep business acumen was either an indication of a rising star or someone that had been around the block a few times.

Questions to ask during an interview:

  • Describe where you see SaaS, as a concept or an industry, evolving to in the next 10 years.
  • Describe a hunch or a prediction in your current role that came true.  
    • How did you communicate that hunch?
    • When it came true, describe the reaction of your peers?
    • What would you have done differently?
  • You’ve gotten to know our business.  Make 3 predictions and back them up.

Fitting the Candidate

There were several other important criteria that Tim looked for in his matrix:

  • Rapid Growth Company – There’s no doubt about it…  the fast pace and ability to make decisions in the absence of data points is a critical ability.
  • Executive Team/Board/Culture/Communications – One could describe this as a test of anyone coming into the organization, but given that this person has to interact with a range of stakeholders on a variety of important topics from hitting revenue targets, to “zero cash day” to payroll, it’s important that you select someone that will fit well.
  • Tech Industry Experience – For us, one of the key aspects of this vector is Software as a Service subscription revenue concepts.
  • Wants The Position/Hungry/Something to Prove – Again, these are good things irrespective of the role.  In the finance function, I’ve now seen a couple of scenarios where a FP&A (financial planning and analysis) person from a large firm was actively seeking are more generalized role in a startup.  The hunger for the exchange of risk for higher responsibility, greater title and a more diverse set of learning experiences is critical.
  • Size of Company – Related to high growth, but different in that a small company requires everyone to wear lots of hats, and usually in a very unstructured environment.  In small companies, everyone has to be willing to get dirty and get the work done.  Candidates from large organizations may say they value this freedom and flexibility, but if their resume reflects only large company experiences, dig deeper here.
  • Managed and Led People Human Resources – Tim really pushed me here.  One of the candidates that we considered hadn’t managed others before.  This function has to manage both internal and external stakeholders to do well.  He asked me several times about my confidence that our lead candidate could step into this capability effectively, or if we’d run into issues with inexperience on this front.


Kicking Off with New Investors – Building Team at Every Level

We closed and announced our $5.25MM Series B in the last few weeks.  It was crucial to me that our shareholders, employees and vendors (which together comprise the Windsor Circle team!) have the opportunity to really engage and build relationships.  So, we created a very intentional and open set of events at the first board meeting with the new investors to really bring the humans involved in this shared journey to the forefront and to really weave the fabric of the team, writ large.

Stakeholders from all aspects of the team commented on how fruitful (and unique) this endeavor was, so I thought I’d share it.  Can’t claim it as a best practice given the sample size of having done it one time, but it “felt” right.  

(In the interest of time, I’m just cutting and pasting the original proposal with some edits)….

———- Forwarded message ———-
From: Matt Williamson
Subject: Windsor Circle Board Meeting Proposal – July 30 Social, July 31 Meeting
To: <*********>

Team – 
As you know, a smooth functioning board is as important to me as a smooth functioning internal team.  So, let’s have some fun and do some good business, too, during this first board meeting, and let’s have a mix of full team and board specific functions.
We won’t go to this depth every time…  but I’d really like to dig deep and get the relationship set nicely on this first one.
So…  here’s what I propose:
Wednesday, July 30 – Social (Full Team)
6:30pm – Happy Hour at WC HQ
8:00pm – Walking Tour of Explosive Growth in the Bull City (Board, Mgmt, Vendors) – I’m working to get Matthew Coppedge, COO of Downtown Durham, Inc. to guide this tour… he can speak to interesting aspects of both the history of Durham and the amazing growth that’s happening right now.
9:30pm – Ice cream social at the Parlour
Thursday, July 31 – Business
7:00am – (Optional) 5k Downtown Durham Run at Marriott Downtown (Anyone)
9:00am – Investor Panel and Bagel Breakfast at WC HQ (Full Team)
10:00am – Board Meeting at WC HQ (Board + Mgmt team)
12:30pm – End
Let me know what you think.
p.s. – Quick side note:  As you know, one of our strongest corporate principles is openness and transparency.  During the panel, you may get really open questions about the process of fundraising, the rigors of high growth, what you’re seeing in the marketplace, etc.  It’s ok to answer very openly.  We talk about things as sensitive as how many paychecks we have left, etc, and it builds really high levels of camaraderie and trust in our team.  We’re honest with ourselves about where we fall down and where we need improvement (in add’n to a lot of celebrating about the great things we’re accomplishing).  Net: we trust each other b/c we work hard on it.  As part of the team, you have full license (and my expectation!) to share your thoughts/perspectives openly.

“Silicon Acres?” Branding the Entrepreneurial Hub of the South

During the Google Demo Days competition, Jimmy Goodmon of CBC New Media shared the story of how his father, Jim Goodmon, had a vision of uniting the several communities of the Triangle (Raleigh, Durham, Chapel Hill) with a centrally located, massive professional sports complex that would capture the two franchise expansions in the NFL and NBA at the time.  Goodmon’s argument was that the combined viewership of the MSA represented by these cities was equivalent to that of Charlotte…  but that we had to pull together.  Ultimately, the three towns and their respective governments couldn’t quite get together the votes to pass this vision, and the idea subsided.

I’m as passionate about Durham as you’re going to find… to the point where my wife and friends sometimes call me “Captain Durham.”  Man, I love the Bull City.  But when I originally wrote this email to then-Governor Bev Purdue about the Entrepreneurial Hub of the South, I bent my vision towards a larger footprint.

I’d like to take another step in that direction.  Branding has such a powerful effect on the formation of ideas and the unification of effort among individuals and groups.  The Research Triangle Park was a brilliant strategic deployment of public-private endeavor in the back half of the last century.  It is thought of, however, as that work place in the middle of the three counties.  Still great.  Still visionary.  But it represents a bit of a fourth locale, not an amalgamation of the three locales that contribute to it.

There is robust entrepreneurial energy, programs, incubators and efforts happening throughout the triangle and enmeshed in the four major universities (UNC, Duke, State and Central).  Another Goodmon (Michael), and his chief strategist Adam Klein, are exploding onto the national scene with the American Underground and AU@Main brands (which has attracted the attention of Google, who has officially named it as a Google Tech Campus).  Innovators like Christopher Gergen are spawning concepts like HQ Raleigh, Bull City Forward and Think House.  Incubators like the Start Up Factory (located in the American Underground) are churning out promising new companies under the empowering guidance of veterans like Dave Neal and Chris Heivly. The energy is off the charts and the sheer power of the job creation and innovation is humming.  You can literally feel it.

I think it’s time we unite our communities in the way that Goodmon originally envisioned with sports, and with the power that the Research Triangle Park brought to NC to attract high paying technology jobs.

As we continue to frame the Entrepreneurial Hub of the South, let’s brand this in a way that is telling of what we do, reflective of our roots, and unifying in the way that allows for each community to thrive in place, but that unites us all.

As the first brainstorming of the brand, I propose “Silicon Acres” playing off the Silicon Valley metonym.  It provides reference to our agricultural roots (of which I am proud).  It also avoids the trappings of locking into a single brand (Bull City, Oak City, etc.).  All of us can be fiercely proud of our own cities, while unifying around a brand that gives us a sum that is greater than its parts.

I’ll toss out a few more:

  • Silicon Triangle
  • Tech Triangle
  • Tri-tech Area

For a bit more depth, here are links to the naming of Silicon Valley and to other locales playing off of this metonym.


The Entrepreneurial Hub of the South

I wrote this email to then-Governor Bev Purdue back in Oct of 2012 after attending an entrepreneur-focused luncheon at the Governor’s mansion. It didn’t go anywhere at the time, but aspects of this vision are being implemented, so I thought I’d post the vision publicly and contribute to the noisy, rambunctious start up process that I love!

———- Forwarded message ———-
From: Matt Williamson
Date: Mon, Oct 8, 2012 at 11:22 AM
Subject: NC – The New Entrepreneurial Hub of the South | Re: N.C. Innovators Entrepreneurs Luncheon
To: “Perdue, Bev” ,

Governor Perdue and Don –

Thank you for hosting. It was an honor to attend.

I’d like to share an idea that maps to much of the conversation. I’ve been thinking about it for two years, but haven’t acted on it as I’ve got this little thing (building Windsor Circle as a start up software company in downtown Durham!) that has been keeping me occupied.

I’ll share the vision here:

NC – The Entrepreneurial Hub of the South

The vision is akin to the concept of the Research Triangle Park in that it creates real reasons to attract talent and resources to NC. It’s a bold vision, much larger than springing up a co-working space or a campus. We need more than that. Every state in the union is embarking on similar incubator programs.

What we need to do is create an environment where the best and brightest innovation talent in the country and the world is relocating to North Carolina to start companies because it is advantageous for them to do so. The following 5 point plan would create that environment for attracting talent:

  1. Leverage Strengths – Strong Universities, Good Business Climate, Great Family Environment for Workers The first part of the vision is to commit everyone to get on message. We have an exceptionally strong academic climate in NC at the collegiate level (we need to work on the school system that feeds it, but that’s a different conversation). The UNC system, plus powerful research universities like Duke and Wake Forest make NC a great place to build ideas and find talent. The business climate is friendly and the costs are low… as said in the luncheon, NC can offer a very cost-efficient climate in which to build businesses. And finally, from a human perspective, this is a great place to raise a family, with beautiful natural resources all around us, and very affordable real-estate. These reasons should be trumpeted to entrepreneurs far and wide as reasons to locate here to build their businesses and their lives.
  2. Build Incentives – Free Work Space, Free Living Space for 2 Years, plus Lifestyle Incentives – As North Carolina continues to shift from agriculture and manufacturing to technology and healthcare, there is an abundance of buildings and warehouses, located in and near downtown areas, often in close proximity to universities of great importance, at rock bottom prices. A concentrated program to stimulate development of these buildings into work and living space would create more than entrepreneurial incubators… these would be havens… communities… tight concentrations of like-minded individuals who want to take risks and create value. Top entrepreneurs worldwide would be offered 2 years of free work and living space if they relocate here (see below). Clearly, you’d start with Durham, Raleigh and Chapel Hill, but once proven, more can be built around the state. Additionally, programs already exist to make it easy for military personel to get lifestyle incentives (insurance, group buying and discounts, discounted entertainment, etc). We could plug directly into this network. (Note the additional benefit of elevating the brave men and women who are risking it all to start business and create employment to the status of those who brave it all to defend our country… this analogy creates massive emotional incentive to take those risks. “She serves our state by being an entrepreneur!” would have the same ring as “He serves by risking it all in the military to defend our country!”
  3. Market “NC Entrepreneurial Hub of the South” to Top Talent Worldwide – Here’s where this becomes more than just a bunch of in-state incubators (which every other state is doing right now, too). We take all of the reasons listed above and hit the road. We get the top entrepreneurs in our state (like Goodnight and Szulik) and hit the road. We pitch the program to the best IT and healthcare students in the top 20 universities in the country and the top 10 in each of China, India and Europe. The goal of this roadshow is to recruit the top talent and ideas to NC. Imagine snagging the best talent that is graduating from Stanford, Harvard, MIT…. from the top universities in Bangalore, in Shenzhen, and other international technology hotspots. The best NC talent (both business and academic) would be identified to chase the best opportunities. If you find a promising healthcare start up in India, perhaps Quintiles CEO would be called in to help recruit the company to NC.
  4. Connect VCs to NC – There are two parts to this. My mentor Ed Paradise at Cisco could help us get telepresence in each entrepreneurial community. All companies would be able to set up powerful virtual board meetings to help shorten the distances that sometimes get in the way of investments here. Secondly, we build and brand direct flights in NC from the major investment hubs as the “VC Jet Set.” We already have direct flights to most of these, but branding and elevating them as a “set” makes it obvious that we’re serious about getting capital here. It’d be a simple exercise to add smaller fractional jet coverage as well. Imagine the power of putting an “entrepreneur only” get with 12 seats together on a monthly basis and putting the most promising companies who are raising money on a NC-funded road show. Consider it a VC highway to NC… worthy of the investment than any other infrastructure would require.
  5. Build “Entrepreneurial Free Trade Zones” – You already have a model for how to create economic incentives with the FTZs that exist in NC. You’d basically create EFTZs to support this program. You’d add the qualification of size, or growth, or investment, or something to make sure you were truly rewarding entrepreneurial companies that had the possibility of high growth and the creation of jobs and wealth.

“NC Entrepreneurial Hub of the South” is a big vision. Over 20 years, we’ll end up developing 30 buildings into Innovators Communities and EFTZs. We’d be on a worldwide stage, driving hard to recruit the very best talent and ideas to our state. We’d be creatively putting NC talent (both incumbent and recruited to NC) in front of the best VCs in the world.

We’d be taking a gamble not unlike that which a group of committed individuals did when they put together a plan for the Research Triangle Park to great effect many years ago.

We’d be displaying the same courageous, innovative risk-and-reward mentality that Entrepreneurs have to summon on a daily basis.

And… if we’re right… North Carolina will be heralded in the same breath as San Francisco, Boston and NYC. Our first goal would be to land in this top ten list. And then work our way to being one of the top 5.

I’m excited about this vision and happy to discuss in more detail.

With warmest regards,


Matt Williamson
Windsor Circle

O: 919.822.2014 | M: 919.724.0931 |
Calendar (Eastern Time) | LinkedIn | @windsorcircle

4 Min Demo | Hot on VC Shopping List | Top Company to Watch in 2012

Thoughts on the National Circles program, and our involvement in it.

The following email was a bit of free form thought processing that stemmed from a dinner conversation with friends about Windsor Circle’s pending commitment to participate in the National Circles program (being implemented locally by REAL Durham, of which Mel Williams is an active contributor).

It involves us making an 18 month, bi-weekly commitment to a single family.  It’s a big commitment.  Thoughts below….

———- Forwarded message ———-
From: Matt Williamson <>
Date: Thu, Jul 24, 2014 at 7:53 AM
Subject: National Circles program
To: ——

Friends –


This is the program that REAL Durham program we were discussing last night.

It’s based on the National Circles Program.
Last night’s conversation was helpful in processing the risk we’re taking as a for-profit entity considering a deep commitment to a family.  As I was reflecting, I thought I’d capture reactions, both positive and negative, as we’ve talked about this internally and externally.
  • Positive Reactions
    • It’s nice to see a company making a deeper commitment
    • It’s a good reflection of who the people in WC are as individuals, and who the company is as a group of individuals
    • This type of commitment is what makes Durham’s brand of entrepreneurship unique.
  • Negative Reactions
    • You might not get out of it what you think you will.
    • Companies may not be set up to deliver these sorts of services, and this could lead to some degree of failure for both the family and the company.
    • This was top down / mandated.  Is WC doing this b/c Matt wanted it done?
    • There’s only 4 people involved in the core group.  What about everyone else?
    • The great white knight…  you think you can ride in and be smart and make change without really knowing the people or the environment.  Lots of examples of this failing at a massive scale.
As I’ve contemplated this effort over the last few weeks, I’ve wrestled with:
  • Why are we doing this?  What attracted me / us to this (versus more standard corporate volunteerism, or volunteerism at all)
  • What are the risks of a for-profit entity doing this versus a non-profit?
  • What’s my role?
  • What do I hope to get out of this?
  • What value am I giving to the family, to the team, to the community, to my company?
I’ve observed, broadly, the following perceptions of businesses and business-types at or near the intersection of poverty issues and trying to address them.  These observations are informed not just in this effort, but also at the helm of various Habitat efforts over the past 20 years:
  • Companies don’t do enough
  • Greedy
  • Too focused on numbers, not focused enough on people
  • Companies / business people aren’t to be trusted
  • When engaged in community effort, company’s have ulterior motives (mostly around taking credit for doing good in a community, even if the good isn’t that impactful, and especially if that token effort is being used to distract from negative community impact driven by the company’s business practices).
I don’t have the answers to much of this.  They’re just observations, and probably skewed as I am one person, with one set of experiences, and I don’t always get it right (I usually don’t get it right).
So, maybe to attempt to answer one of my own questions….  Why are we doing this?  What attracted me to this?
I’m attracted to the National Circles program for two reasons.  
First, the model is showing quantifiable success in alleviating the conditions of poverty.  It’s early.  We’ll see if these numbers hold, but I can’t deny that I’m interested in programs that can show real progress.  And I care about my community, and the people in it, so I was attracted to the effort because it could make a difference in my community.
Second, I’m intrigued by the level of commitment and connection being implied here, and that no company to our knowledge has attempted this.  There’s nothing wrong with the team volunteering once a quarter (and we do).  But this is about getting involved with a family in our community…  in my community… every other week for 18 months.  Not painting walls…  Not picking up trash…  (we do that already and are happy to do it more)….  But opening ourselves to what may be some painful introspection about the disparities in our community.  Being vulnerable during the training to be told just sit there and listen…  that your family leader is going to be smarter/better/more capable than you are at directing what will make change in their lives and in their communities.  To risk becoming emotionally connected to others who live very different lives, and wrestling with what that may entail in our own lives.  To deal with the unpleasantness of being perceived as a person of privilege that is doing this for the wrong reasons (this one is particularly hard for me to digest).  And, maybe, if we risk that much commitment, a family in our community may make real progress in their own journey.  And, as this unfolds, we as allies to this family might make real progress in our journeys as well.
I don’t know where this will go.
I’ve been a bit surprised by some of the negative reactions to attempting this.  On the face of it, one would think that a group of people, organized for whatever reason, who wanted to help implement a program that is showing real success in other locales would be a good thing.  There’s something about the fact that our group of people happens to be organized as a company (versus a civic organization or a church group) that seems to make people uncomfortable.  Maybe it’s in the way that I’m presenting it.  Maybe there’s an inherent distrust of corporations (and perhaps well earned).  Maybe corporations can be good at creating opportunities for its individuals to do good work, but that they are inherently poorly suited to engaging in that work directly.  I don’t know.
All this said…  entrepreneurs take risks.  I think we’re going to give it a go.  It’ll be an interesting journey, with an uncertain outcome.  But I’m excited to be trying, and I’m pleased that the people in my company are the types that would even consider it.

The Weekly Planning Sheet

Years ago, I spent some real time digging into Stephen Covey’s 7 Habits of Highly Effective People.

In quick summary, his thesis is:

  • He studied a bunch of very successful people (not just financially, but those w/ high degrees of respect in their community and having accomplished interesting things but not at the sacrifice of their families and friends).
  • He tried to isolate what was similar in how these people lived their lives (hence the 7 habits, see below, copied from wiki).
  • In essence, these people think of their legacy, plan long term objectives that are in line w/ the legacy they want to leave, and then proactively take action against them.  He suggests a weekly planning framework to operationalize this thesis.

It’s been very effective for me personally.  I’m not a “Covey-head,” and won’t project that it works for everyone in all cases.  But I do know that most of the interesting accomplishments in my life have been because I was thinking about the person I wanted to be remembered as when it’s all said and done, what creative and fun life experiences I wanted to have to get me to that place, and then having a plan for taking action to drive me towards those goals.

My Most Recent Tracking Spreadsheet

Over my career, I’ve swayed back and forth between good usage of the methodology and not using it.  In this most recent return to the methodology, I built it Google Spreadsheets and discipline myself to spend time each week.  I’m not perfect at it, but it helps to keep things balanced when I do.

Here’s my sheet: 7 Habits Tracking Template


In case you’re curious….

7 Habits of Highly Effective People (taken from Wiki)

  • Habit 1: Be Proactive Take initiative in life by realizing that your decisions (and how they align with life’s principles) are the primary determining factor for effectiveness in your life. Take responsibility for your choices and the consequences that follow.
  • Habit 2: Begin with the End in Mind Self-discover and clarify your deeply important character values and life goals. Envision the ideal characteristics for each of your various roles and relationships in life.
  • Habit 3: Put First Things First A manager must manage his own person. Personally. And managers should implement activities that aim to reach the second habit. Covey says that rule two is the mental creation; rule three is the physical creation. Interdependence
  • Habit 4: Think Win-Win Genuinely strive for mutually beneficial solutions or agreements in your relationships. Value and respect people by understanding a “win” for all is ultimately a better long-term resolution than if only one person in the situation had got his way.
  • Habit 5: Seek First to Understand, Then to be Understood Use empathic listening to be genuinely influenced by a person, which compels them to reciprocate the listening and take an open mind to being influenced by you. This creates an atmosphere of caring, and positive problem solving.
  • Habit 6: Synergize Combine the strengths of people through positive teamwork, so as to achieve goals no one person could have done alone.
  • Habit 7: Sharpen the Saw Balance and renew your resources, energy, and health to create a sustainable, long-term, effective lifestyle. It primarily emphasizes exercise for physical renewal, prayer (meditation, yoga, etc.) and good reading for mental renewal. It also mentions service to society for spiritual renewal.


Should you work at a Start Up? (Cross post from Bessemer)

Note: This article, originally in Venturebeat and cross-posted on the Bessemer Venture Partner’s website was so spot on that I’m quoting it in it’s entirety.  

Source: Bessemer Venture Partners Blog



Should you work at a “start-up”?

January 2014

This article was originally published by Venturebeat

I recently made the switch from start-up to VC, joining BVP after three years as part of the team at Foursquare. Recently, people have been asking me a lot about my experience switching careers and what they should consider when thinking about transitioning into the start-up world. Over the course of these conversations, I’ve boiled it down to four questions that I think are worth asking yourself before taking that leap…

1) What is your definition of “start-up”? – The phrase “start-up” can be misleading, describing businesses in many different stages. Be honest with yourself about the level of risk you’re willing to take – do you want to join a company with traction, financial runway, and one that will give you the opportunity to learn from experienced people, or do you want to join an earlier stage company with more potential upside, but more uncertainty? Your experience will largely be based on the company’s size, financing history, and experience level of the people you will be working for and with. With just 20 colleagues and less than $2M in funding, Foursquare was a different company when I joined than the company that I left three years later with 170 employees and over $100M raised, but it was definitely a “start-up” throughout

2) Why do you want to work there? – If you’re thinking of joining a start-up because it sounds cool or your roommate is doing it – don’t. Make sure you think the company has great leadership and a product or service you can get behind. Sure, the offices will likely be a fun place to spend your days compared to your current corporate digs (and there might even be beer on tap), but things aren’t always easy when dealing with the ups and downs of an organization finding its way. Make sure you are excited to be in that space going forward, as you will likely be gaining expertise that will guide what you do next.

3) Are you ready to define your role? –  The earlier in the company’s life, the more you will have to dictate how you spend your time. Earlier stage start-ups have an endless number of things they could be doing. No matter what your role is, it will be largely up to you to prioritize your time and figure out how to add value. Nobody will be holding your hand or giving you constant feedback, so understand that is what you are signing up for.

4) Have you cut through the hype? – If you want to know how well a company is really doing, what it’s like to work there, and whether or not it’s a good fit for you, then you need to talk to current and former employees. One thing you learn quickly while working at a start-up is that there is often a massive disconnect between perception and reality. So get connected or introduced to people who know the real story.

At Foursquare, I was lucky enough to work with smart, passionate colleagues, experience rapid growth and the associated growing pains first hand, and witness fundamental product and strategic shifts. It was an amazing team to be a part of and the operating experience has served me well in my early days of working with entrepreneurs. If you can get comfortable with the answers to these questions, then go for it.

Foursquare team meeting, June 2010 (photo by Mari Sheibley)

– See more at:


The Culture Sandwich

We have an informal professional development thing going at Windsor Circle.  The group chooses a book, company buys copies for everyone that wants to participate, and then we meet for several weeks and discuss the book as we progress through the chapters.

In a recent conversation, we discussed at length how culture is set in an organization.

In most cases, the culture is set by the leaders.  If there’s apathy at the top, it will flow throughout.  If there’s a solid set of principles, well applied, that too will propagate.

But the thing that I found interesting was how the team at large receives and amplifies the culture.

Initially, the leaders set the culture at the top.

But then that culture gets codified into systems and practices.  At Windsor Circle, things like the quarterly team day and our Friday Sales Meetings are examples of things that codify the culture.  At this juncture, we’re still small enough that our team has regular interaction with our leaders.  The culture can be communicated directly.

As we scale, however, that culture will not be directly interpreted from my mouth.  As we scale to 100 people, or 300 people, or 1,000 people, the culture will actually come from the bottom up.  People will interpret the culture from the people around them, and the systems that support them.

In essence, you have people at the top setting culture, and people at the bottom setting culture…  and what lies in between is the true test of what a firm is made of.  A culture sandwich.

It reinforces how critical it is to document and constantly refer to one’s principles and then find ways to cement them in via routines, practices, and events so that large groups of people interpret and reinforce the culture in the same way.  Failing that will surely lead to a disjointed and apathetic organization.



5 Critical Components of Building A Winning Startup Team

This week I was invited to speak at an entrepreneur’s only lunch hosted by CED, on the topic of building winning teams in a startup environment.

The attached presentation highlights what I think of as 5 Critical Components of Building a Winning Startup Team.

CED Entrepreneur Series Nov 2013

  1. Founding Team – Share Equity and Play Fair
  2. Commander’s Intent – Capturing Vision, Mission and Principles
  3. Know Thyselves – Personality Profiles with Myers Briggs
  4. Be Big Now – Ruthlessly Repeating Who You Want to be Tomorrow, Today
  5. A Little Crazy is Good – Tapping into Creativity, Spontaneity, and Uniqueness

The presentation contains specific examples from our experience as a startup (although you’ll have to forgive a few greyed out areas to protect confidentiality).



The Power of Myers Briggs for Start Ups

We hold a quarterly team day to ensure that we are nourishing our most important asset…  our people.  In an entrepreneurial environment, it can be hard to come up with the resources (cash, expertise, time) to create meaningful exercises that dramatically accelerate a team’s ability to form and perform, beyond the stereotyped foosball table and free sodas.

Don’t get me wrong…  we have our Friday Sales Meeting (a weekly all-company happy hour where you have to pound your tasty beverage if you are caught talking about work) and we regularly get the team together for outings like the Thanksgiving Texas Hold’Em Smackdown or the July 4 “Grill ’em.”   But these are social events, intended to be casual, easy, and free flowing.

At Windsor Circle, we actively engage each team member with a Myers Briggs Assessment and then spend 2-3 hours going through exercises to understand how various types of people interact, and how it applies to the people in our team as they express those personalities.


  • Human Metrics has a quick and free assessment here.
  • Typelogic has good descriptions of the various types here.
  • John Fahlberg, a retired Target executive, has coached us numerous times on this disciple.  If you’d like him to coach your team, visit his site, and tell him I sent you.


Just to get the juices flowing, I thought I’d summarize some of the comments and observations from our experience yesterday.

  • 100% Intuitive, 0% Sensing – This vector has to do with how people take in data.  Sensing types do a lot of research, and then shape their world around the existing data.  Sensing types seek “what is.”  Intuitive types engage high level concepts and patterns, placing high importance on imagination.  Intuitive types seek “what could be.”  It was fascinating to find that in our team, we were 100% “what could be.”  We theorized there was a selection bias here…  that the startup environment attracted those who loved the art of the possible, and that the risk and unknowns of the very early stage process might drive those who seek data and structure away.  It also made us think about next hires…   might be good to balance us out a bit!
  • “I hate being praised publicly” – One of our engineers, who has a strong expression of introversion, shared with me that he not only didn’t care about being praised publicly for doing well, that it actually made him uncomfortable.  A well meaning extravert (like me) might sing his praises in a team meeting, completely unaware that this is actually a painful experience.  What this specific team member expressed was that he was much, much more motivated by being given a thorny technical problem to solve and the time to solve it.  Unlocking his zeal and passion for Windsor Circle, therefore, is much more about planning and allocating tasks than it is remembering anniversaries or publicly praising him.
  • Brad’s Time of the Month and Carrie’s Internalization – My co-founder, who runs sales, holds responsibility for client renewals.  During our monthly billing cycle with clients, there are always a few that raise their hand to cancel their contracts (primarily for non-usage on the clients’ part).  And it drives Brad batty.  He wants our clients to be successful.  He wants Windsor Circle to be successful.  And when he processes a few calls / emails in one day (triggered by the billing) he gets grumpy.  Under stress, his personality type (ENFP) feels overextended and edges towards shutting down.  One of his team members, Carrie, has a high social component to her personality type (ENFJ), and therefore internalizes others’ stress.  They discovered that when Brad is in “his time of the month” that she also feels stress because she’s wondering what she has done wrong.  Knowing the pattern will help them operate more smoothly.
  • I Get Irritated by Those Who Won’t at Least Consider the Impossible – The book that we’re using details each personality type, and describes what irritates them and how they may irritate others.  Two strong traits of mine are that I am drawn to things that others haven’t done before, and that I deeply believe that they can be accomplished with enough vigor, passion, intelligence and hard work.  I have a very strong negative reaction to those who look for reasons why something won’t work instead of inventing innovative ways to actually pull it off.  In reading my personality type handout, I discovered that it’s a known phenomenon that us ENFPs get irritated “by those who won’t consider the impossible”.  And, interestingly, other personality types may become irritated by an overly optimistic and unrealistic approach to new projects that my personality type expresses in extreme situations.  The awareness of types is what’s important here..
  • I Need Time to Process – My co-founder and CTO, Chris, is a strong INTP.  He draws energy from having time to center, without distraction, and process things.  His predilection towards logical, data driven, non-emotional information gathering and decision making means that in times of high stress, he needs time to go process things.  My personality type in the same situation requires high degrees of social interaction and group brainstorming.  Both approaches are fine…  but under stress, operating without an understanding of what the other person needs is a recipe for conflict.  Here’s a post about a specific experience that started off hard but ended up bringing Chris and I even closer as co-founders.

We uncovered a lot of other interesting insights during our session.  I hung the resulting charts in the kitchen area so that our team will see where we landed, how we interact and perceive the world, and how to engage one another in ways that will help us out-compete those who are not specifically working to build their teams with the intentionality that we are.

I’m excited to be blessed with a team that works so well together and trusts each other with personal perceptions and sensitivities.  It was amazing to me how often a team member would speak not only about how their personality type may become irritated by others, but how often they named how they might irritate others.  That high trust is the hallmark of a good group of people who are pulling together to excel at a shared task and who are investing in each other.