Deep Dive Mini Series: Avoid These 5 Deep Dive Meeting Pitfalls

This article, adapted from a post originally published by the author in Inc. Magazine, is the last in a three part mini-series on deep dives. You can go back and read the first article here.

Avoid these 5 deep dive meeting pitfalls
Image by John Maffei

If you are coaching a team that knows what a deep dive meeting is and how to prepare for it, then it’s likely they also know how to navigate their way through it so they can move forward with investors into and through due diligence. All that is left for you to teach them is how they can avoid undermining themselves during the deep dive meeting itself.

Traps for the Unwary

We’ve talked about the importance of building rapport as a key function of the deep dive meeting. If there are ways to build rapport, there are definitely ways to destroy it. These traps are distressingly easy to fall into for a stressed-out person under a lot of pressure. However, with a little coaching preparation, some self-awareness, and some knowledge of the issues, it is possible to teach a team to avoid them.  

Teach Them to Be Strong, but Have Some Humility

Investors are searching for founders with spine and a clear vision, and the tenacity to be successful. But they also want someone with some self-awareness and humility. Investors prize what they call coachability. Trying to be a know-it-all will put a very deep chill on the mood in the room. Coachability is not about being a wet noodle, open to every suggestion - it is about being willing to listen to and engage different views, and even taking a bit of good advice here and there.  

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Remind Them Not to Lose Their Cool

Another very negative dynamic can occur when investors feel that the entrepreneur is failing to listen to the question and answer directly. Similarly, becoming flustered and lacking poise and grace under pressure will worry investors. Conversely, dealing with feelings of frustration or covering up insecurities by being argumentative or combative is also a very bad idea. The investors have showed up because they are impressed with the team and are interested in their company. Tough questions are a sign of curiosity and respect. Remind a team that investors are not asking to trick or trap them, they are asking because they want to know the answer. And, if a question relates to something that is just unknowable at the present stage of the company’s development, it’s ok to just say so. There is no need to be defensive or hostile. No one expects a team to be perfect or to know everything.  

Alert Them to Watch Team Dynamics

There are also some team traps that are easy to fall into when a CEO brings co-founders to the deep dive meeting. These traps generally fit under the heading of team “choreography” mistakes. Although many CEOs choose to just show up alone (which can work, provided you have a good team slide), there are some advantages to showing off a great team. To make it work to a company’s advantage, they need a plan, and lots of prep to nail the execution. Here are some traps to avoid:

Keep Team Members from Rambling

The first issue is co-founder verbosity. Be forewarned. Co-founders need to be very brief and stay on script. Even in the best case, brief interruptions and transitions are disruptive to the flow of a meeting. If they are long-winded, it can be a disaster. It can cause a loss of momentum a team cannot easily get back. Do the prep necessary to keep co-founder answers short. Sometimes co-founders have been bottled up so long they start rambling and over-answer (this can be acute, for example with technical co-founders who preside over very complex subject matter). 

Know Who Is On Point

It is also important to prep on the ownership of topics to avoid the pitfall of not knowing who should answer which questions. If multiple people jump in and talk over each other, investors will wonder who is in charge (and why they didn't prepare better). Generally, the best plan is to agree that the CEO will take all questions EXCEPT those on specific topics. Then agree exactly what the answers to those topics are going to be and practice them until they are fast, tight and on point.

Beware the Contradictions

Similarly, contradicting each other makes investors wonder if the team is on the same page. Or, worse, they might think team members are covering something up or not being totally forthright. The same is true with steamrollering over a co-founder trying to answer. Both make people wonder if the CEO is a good manager or commands the necessary respect if he or she has to be brusque or harsh in managing a co-founder.


Coaching for deep dive success is not easy. These meetings are tough. The main reason is because there is nowhere to hide. The process is a long, unstructured, Q&A meeting with the outcome potentially having a major impact on the company. That is a high pressure situation. Being prepared is essential. Knowing ahead of time how to navigate the deep dive through the interactions will help you get the team ready. And finally, teaching them the importance of mastering their choreography and body language during a deep dive is critical to a successful outing.