The 2 Day Board Meeting: Speed Dating, Texas Hold ‘Em, and Green Pants

Investors in Green Pants
Windsor Circle Investors Rocking the Green Pants

At Windsor Circle, we define team not by who is on the payroll or inside our four walls, but truly by everyone who is working to build the Center of the Retention Automation Universe.

This includes our employees, our service providers (attorneys, accountants, landlords, etc.), interns, and most certainly our investors.

We have worked hard to find investors who share our values, see the same opportunity that we do, and who could add far more than just their dollars to our efforts.

The Two Day Board Meeting…  What the?

Believe it or not, we hold a two-day board meeting every other quarter.  We do this because we want to unlock the collective experience and insights of a talented set of market makers, and feel that you can’t do that with an 3-hour board meeting where all you are doing is giving updates.

We do a financial call two weeks prior to the meeting to get all of the updates done, and to provide 2 weeks of time for the board to think about the data.

The board meeting itself is held onsite, spans two days, and is driven specifically by two main objectives:

  1. Strategic Thinking – We aim to make the board meeting itself a 4 hour conversation.  No board deck, no updates.  We did that in the financial call…  this is about collective thinking, problem solving and “strategery.”
  2. Team Building – We make certain that our entire team is interacting with one another.  Investors, associates, and management team members meet, socialize, share ideas, and solve problems together.

Our March 2015 Agenda

Click here to download our full agenda for this last board meeting.

Here’s a quick summary:

  • Day 1
    • Speed Dating – We needed to help our investors get really deep on the opportunities for both expansion and improvement, and we wanted to expose them to a larger number of our team members, so we created a 3 hour Speed Dating experience.  We had 6 stations, each staffed by 2-3 associates who took them deep on a particular part of the product or the go-to-market strategy around the product.  They had 20 minutes to listen, learn, take notes, and ask questions, and 10 minutes to transition.  In 3 hours, each investor had rotated through all 6 stations in an intimate setting, with the opportunity to directly observe our company and our product for all that was good (and not so good!).
    • Executive Dinner – We made sure that there was time for the investors to build relationships with the management team, and even kept it super healthy (salads and light fare).
    • Texas Hold’em Tournament – That evening, we put away the work stuff and had an all hands poker tournament.  It was a ton of fun to watch a total of ~35-40 engineers and investors, marketers and management, sales and client success all squaring off in a fun game of Texas Hold ‘Em!
  • Day 2
    • Executive Breakfast – This was a second opportunity to deepen executive and board level relationships.  We made it optional, but everyone showed up.  While the dinner the night before was more social, this was a little more structured around strategic conversation and digesting information learned during the Speed Dating sessions.
    • Board Meeting (No Updates…  All Strategy) – This was the big test. We purposefully built no board deck, which felt a little awkward, but it was really freeing.  We had data on hand that we could pop on the screen to answer certain questions, but largely, this was 4 hours of fantastic strategic conversation.  The strength of our investors and advisors really shined through during this session.  We had well connected, deeply educated and experienced people working side by side with us to solve problems and exploit opportunities.  It was quite an experience
    • Investor Panel – After the board meeting and lunch, we held another all hands session, this time in the format of a town hall / panel style interaction.  The investors (now all clad in Windsor Circle Green Pants!) sat up front, with the entire company in the room.  We instructed our company that no question was taboo, and likewise instructed our investors to pull no punches.  Openness and Transparency is a key value for Windsor Circle, so these instructions were well heeded and we had a fantastic and honest conversation as a cohesive team about what the market looked like, what opportunities and threats Windsor Circle has, and what lay ahead for us as we continue our very rapid growth as a company.
    • People Helping People – Opportunity to Pitch to Our Investors – We sought commitment from our investors in advance to spend time with fellow entrepreneurs in our ecosystem here in Durham.  We basically created the opportunity and then got out of the way, so our peers could have direct access to our investors to pitch.  We understand that this was well received by both sides!

One of the Best Board Meetings!

All of our investors reported back that this was one of the best board interactions they’d had in a long time.  Here’s a quick quote from one of our investors.  (Sidenote:  I share this quote not to be pretentious, but rather of evidence that this calculated risk regarding the extended meeting format met with the results we’d hoped for).


Good meetings on Wed & Thurs.  You are the first CEO, in my experience, to successfully pull off a separation of ops and strategy.  Other CEO’s & boards have recognized the value of doing it but most of the time the strategy session devolves into ops anyway, or the strategy is pushed to the end of the meeting and some of the folks have already left.”

If you’d like to download the board agenda for more specific details, click here.

How Rockstar Leah Houde (Executive Director, Duke CE) Helps Execs Handle Difficult Conversations

Every quarter, Windsor Circle holds a “Team Day,” where we leave the office for a day and do three things:

  1. Volunteer in our community,
  2. Learn about “the science of teamwork,” and,
  3. Goof off a bit at Bull McCabes, our favorite watering hole.
Leah Houde, Executive Director, Duke Corporate Education

In this last science-of-the-team session, we enlisted the services of Duke Corporate Education, and specifically the talented Executive Director, Leah Houde.

Duke CE (located right here at the American Tobacco Complex in Durham, NC) typically coaches CEOs of F500 companies, and has been named by Financial Times as the best corporate education group in the world for 12 years running.  (Yeah, wow… mad props).


We wanted to arm our team with the tools necessary to have difficult conversations so that when the rigors of building a venture-backed business raised peoples’ hackles, that we’d know how to navigate hard conversations like bosses.  Here’s a quick summary of what we learned:

1. Mind the Gap!  (Inner Voices)

Imagine the following conversation:

CEO: “We’re going to triple the business this year!”

Employee (says out loud): “Right on!  Let’s do this thing!”

Employee (inner voice says): “Good lord…  how are going to do that?  And my quota is going to go way up.  This sucks and I’m scared!”

The gap here is palpable.  If the CEO isn’t actively listening and creating opportunities to get closer to the inner voice, she or he has a real problem.  The employee is rightfully showing enthusiasm and support.  The CEO is hearing agreement and buy-in.

But what’s really happening here is that the employee is feeling really scared about the change that is coming.

Here’s another example, from Leah’s presentation.

Source: Leah Houde, Duke CE
Source: Leah Houde, Duke CE


It’s important to do two things here:

  1. Mind the Gap – Just be aware.  We all have that little voice inside our heads keeping a running commentary of our lives, but if there’s a gap between what’s being said aloud and what’s being thought, you could have a serious disconnect.
  2. Create Room for Inner Voices to be Heard – In the short term, this could be providing for truly anonymous surveys or feedback mechanisms.  In the long term, it should be continuing to make deep deposits into the emotional bank accounts of employees and earning their trust over time.  The more genuine vulnerability and earnest attention to people’s opinions you can show, the more the gap can shrink, because people feel that they can trust you.

Remember, the bigger the gap, the bigger the problem.  Work hard to listen for that inner voice.


2. Intent vs. Impact

This is a big one.  Inside our own minds, we have years of context and conditioning.  We are masters of our own data and experiences.  So when we act, or make a statement, we do so with all of that context…  in other words, we intend to communicate a certain sentiment with the words we choose, based on what we know.

But this is problematic, because the person you are communicating with may not share your context.  They may not know what you know.  And so the impact of what you are saying may miss the mark.

Consider the following:

Prospective hire: “So, as a startup, how profitable are you?”

CEO (enthusiastically): “We’re not profitable at all, and have no plans to be!”

Prospective hire (inner voice): “I gotta get out of here… this is a sinking ship.”

In this exchange, the prospective hire is equating profitability with job security.  The CEO of the startup is excited about not being profitable, because in a high-growth, SaaS business model, if all of your other metrics are right (CAC, margin, churn, and growth rates) the last thing you want to do is slow down and try to get to profitability.  The explosive growth and lack of profitability, to the CEO, is a sign of rampant success!

In this scenario, the CEO would have been better served to ask “Great question…   Are you asking about the nuances of our SaaS operating metrics, or are you more concerned about our success and survivability as a firm?”  This would have aligned intent before the impact of a grandiose statement scared off this prospective hire.

Remember that your intent is tied to your own contexts.  Ask clarifying questions early and often when communicating so that the impact is what you wanted it to be.

3. Walk Me Down Your Ladder (of Inference)

Source: TedEd
Source: TedEd

Argyris (HBS) and Schon’s (MIT) Ladder of Inference is a construct for understanding how we as humans frame perceptions based on data that we have.

We observe data (bottom of ladder), apply reasoning based on our experiences and knowledge (middle of ladder), and then come to a conclusion (top of ladder).

We as humans evolved over millions of years to get to conclusions very quickly… and that’s healthy.  Those who couldn’t quickly surmise that fast things with large teeth were likely to eat them, were removed from the gene pool.  Those who could quickly arrive at this conclusion (“Danger!  Run!”) passed along this hard wiring to their progeny (us!).

So… relax.  It’s healthy that we quickly and automatically form conclusions.  We just need to be aware of them, especially when our conclusions are causing conflict.

Using the prior example, the CEO is working from a data set that is framed by years of executive experience in SaaS.  She has seen scores of examples of high growth SaaS businesses produce significant wealth by specifically not trying to achieve profitability, but instead by focusing on growth within the right SaaS metrics.  The prospective hire on the other hand, may have been a part of businesses that failed because they were poorly managed, did not have access to funding, and did not achieve profitability (self sufficiency)… and as a result felt real pain when they were laid off.

In other words, these two participants are talking about the same thing, but working from different data, processing that data in different ways, and ultimately reaching different conclusions that are in conflict with one another.

What’s useful about this paradigm is that it lends itself to a phrase that can be invoked when you are in conflict or disagreement with someone.  

“Hey, we’re seeing this differently.  Will you walk me down your ladder and help me understand your data points and your experiences so that I can understand the conclusion you are reaching?”

I started using this phrase, “walk me down your ladder,” almost immediately in our business and to good effect.  Yes, it’s a bit cheesy.  Yes, it feels a bit “corporate” to say “walk me down your ladder.”  But the benefit of clearly signaling that you care enough to try to understand the other person’s perspective, and that you’re willing to risk some cheesiness and business-speak to do so, is well worth it.

[Update: Since writing the initial draft of this post, I’ve had multiple Windsor Circle employees actually come tell me that they are using this technique all of the time, and not just at work.  One of them shared that he and his wife were in a heated argument, and he said, “this is gonna sound dumb, but walk me down your ladder.”  In a matter of minutes, they realized that they were arguing over nothing, and that by taking time to review their assumptions and underlying observations, they resolved the argument and got themselves back to a fun place instead of an angry place.]


We are targeting significant growth in 2015 at Windsor Circle.

We held a company wide meeting and specifically invoked these themes.  We acknowledged the inner voices of our team, who have largely not been in venture-backed, high-growth start ups before and who have not seen this sort of aggressive growth in their early careers.

We did this with phrases like:

 “It’s ok to be nervous about these big goals and these changes.”

“The big targets are going to mean a lot of hard work, a lot of risk, and indeed, some failure!   And that can be scary.”

“Those of you on variable compensation targets, primarily sales, are concerned because your quotas will go up.”

We then literally used the words (because everyone was trained on them), “let us walk you down our ladder so that you can see what the management team and the investors see, and then we welcome you to draw whatever conclusions you’d like from that data and reasoning.”  Certainly our hope was that our team would see what we see, but our goal was to align, not necessarily to convince.

Given the Windsor Circle core values of “openness and transparency,” and “facts, not claims,” we showed specific numbers to our entire team regarding the funding that we’re putting to work to make these growth goals a reality.  We showed how dramatically we’re ramping the product team, and the investment in the marketing team.  We showed comparison charts of how much more we’re investing in marketing spend and in which channels.

It doesn’t mean that people immediately snapped out of their own conclusions… that would be a silly expectation on our part as a management team.  But by earnestly listening to inner voices, thinking about our intent and impact, and using the framing of “the ladder of inference” we shifted the conversation away from the fear of the unknown, and over to a reasonable discourse of why all of the data suggests that this is the right time, and the right team, with the right resources, to get this done.

We just ended December at 151% of our best month to date, and Q414 at 142% of our best quarter to date.  We’re three weeks into January and we’ve already beat December.  We’ve got a lot of wood to chop in 2015, but I think we’re headin’ in the right direction!

Thank you, Leah and Duke CE, for being a part of our journey.  These are invaluable tools and we appreciate you helping us learn and leverage them.

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.