CEO: Teach Your Team How To Debate

Your #1 job as a leader—to create other leaders.

One of your many jobs as CEO is to make the company a safe place to debate and to moderate (and participate) in those heated discussions. You will also likely have to teach others on the team how to debate given our current dependence upon technology which has resulted in a lack of in-person communication with a high desire for harmony. I find that many startups today are filled with people who are extremely conflict-averse and require encouragement and mentorship to add value to the many debates.

Think about the never-ending set of debates you had in the beginning when your tech startup was simple… What problem did we solve? Who else was having the problem? How big of a problem was it at the time? How did others solve the problem? What was our value proposition? How did we reach those customers? What were the must-have features versus the nice-to-haves? Did a certain feature prove product-market fit?

John Wooden–“Men, this is how you put your shoes and socks on.”

Like John Wooden, you are going to have to teach your team the basic elements of debate… Possibly use the example of the premise your company was founded on… For example, your company was probably built on an idea (a claim), with supporting evidence that provided an inference that your claim was true—these 3 elements were the foundation of your company’s first debate. If you deconstruct Airbnb as an example (see pitch deck) you will see that the idea (claim) was that the world needed a web marketplace platform where users could rent out spare rooms (to make money) to travelers (that would save money and share in the culture of the city) so they didn’t have to stay at high priced hotels.  The supporting evidence offered to the investor was that at the time there were 630K users on the temporary housing site couchsurfing.com, 50K temporary housing listings in the USA per week on Craigslist, 2B trips booked world-wide each year, 560M online trips (Serviceable Available Market) all inferring that with events, partnerships and Craigslist dual posting, an easy to use web marketplace with a host incentive would allow them to acquire 10.6M trips & 200M in revenue.  You can imagine how the debate might go with the typical ventral capital group…

Help the team see the variables within the debate:

  • The claim is the statement that the person on the team is making and wants their audience to accept.
  • Supporting evidence is a set of ideas the audience accepts as true.  This evidence provides the foundation for acceptance of the claim.
  • The person making the argument wants to move the audience from what they believe (the supporting evidence) to what they don’t yet believe (the claim). The magic happens when the audience discovers the connection between claim and the supporting evidence–The discovery of this connection is known as the inference.

Then help them understand where the complexity of the debate begins… Supporting evidence is usually a claim to be proved. For example, how do we know ‘Price is an important concern for customers booking travel online’–This seems obvious but how do we know this is true?

Sometimes it’s easier for the team to see the framing of the argument visibly:

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With this context, you can teach your team how to frame arguments and also poke holes in a weak hypothesis.   In framing, they need to know how to take the argument as deep as it needs to go by being prepared for counterpoints.


They also need to be prepared for the generic “bomb” on all the other reasons this argument does not make sense. For example if a generic counterpoint is made that is not in reference to a supporting point–the team needs to be prepared.

When you look at an argument visibly and go several layers deep on each and every claim and counterpoint you might start realizing how many critical decisions are getting made in your company with assumptions versus with the right level debate or all the necessary data.

As the team gets better at internal debates they will learn the difference between descriptive (definition of things), relational (the relationship between things), and evaluative (value of things) arguments and how to break down or support each using an efficient strategy.   

You can use tools like 5 whys and the 6 Thinking Hats as great ways to open your team’s eyes up to both the depth of an argument, as well as, the efficiencies within the argument.  Another great tool is the use of Precision Questioning where you can help your team know what’s expected in regards to supporting evidence to back up claims. The basics of Precision Questioning starts with how to use different types of questions as follows:

  • No-Go: Why is now the right time for this idea (claim)?
  • Clarification: What do you mean?
  • Assumption: What assumptions you are making?
  • Data: What’s the quality of the supporting evidence?
  • Causes: What’s causing the opportunity (a problem in the market) that your company will address with its solution?
  • Consequences: What happens if you are successful? What happens if you are not successful? What are the possible side effects? What are the opportunity costs?
  • Actions: What should really be done to solve this problem? What specific time-bound steps will everyone take? How does this align with other initiatives?

…and most important of all, ensure your team knows that what works as a debate tactic in politics (fear, lying, bluster, vulgarity, innuendo, and refusal to admit your wrong) does not work in a startup and you as the leader/moderator of most early debates can’t let it into the discussion.