If Something Feels Off, Don’t Ignore It: Assess the Leadership Team Before You Buy
By Jennifer Mondoux
October 7, 2025
"Is this the group of people who will take me to my investment thesis?”
It's the question all investors should be asking when looking at the leadership team of a target acquisition.
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Why devote resources to due diligence on everything else – finance, operations, etc. – but NOT on a thorough examination of the leadership team? The ones who do take the time – and devote a portion of the budget – to assess the leadership team pre-transaction are usually the ones who have learned from past experiences. Others cross their fingers, even though they know something is off… The reality is this: if you are sensing problems with the leadership team during regular/financial due diligence you should pay attention to how you feel. You are probably right. And rarely are those problems simply going to go away once the deal is done...
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To be clear, when we talk about leadership due diligence we are not talking about an HR assessment which is more about compliance. Leadership talent due diligence is a very different exercise.
Here are some best practices:
Work with a trusted partner: Choose someone who is experienced, in particular at interviewing and assessing people. Someone who can build rapport and trust. Whoever you choose, they should probably be 3rd party. It's not fair to ask HR to do this as they are too close to the situation.
Don't do a group interview: This is the worst idea and if it is suggested to you, shoot it down. No one will be comfortable nor will they speak openly. One-on-one interviews, in a quiet confidential setting, are key.
Don't limit the assessment to interviews focused solely on competencies: Ask SWOT-related questions to each person on the leadership team. They will be much more engaged and if the right conditions are created they will use the opportunity to get their message out. Most do this professionally.
Complement the interview and SWOT with 360s and psychometric assessments: 360s have famously had a bad rap but there are new automated tools in the market and the insight you can glean is incredibly helpful.
Communicate the exercise in advance: Ideally, the CEO of the target gets the buy-in from the team. Encourage transparency, and pitch it as an exercise to make the organization better. Commit to playing back uncovered themes where possible.
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Rarely have we had an investor client say they're not moving forward because of what we've uncovered in an assessment. And that's not really the point (unless it's something drastic). They feel more armed with information, and that increases confidence. Some even put conditions on the offer – e.g. executive coaching for a CEO, leadership development for a high-potential, etc. In fact, a good assessment should come with these types of recommendations.
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If something feels is off, don't ignore it. Ask for an independent assessment. Know what you are walking into so as to not risk the ROI.
About The Author, Jennifer Mondoux:
Jennifer Mondoux, CEO and Managing Partner, MondouxRollins Partners Inc.; Chair and Founder, Canada’s Best Private Boards
Jennifer Mondoux is an executive search professional and human capital advisor, with nearly two decades’ worth of experience working with private companies. An exceptional search professional, she has helped dozens of founders and entrepreneurs of mid-market companies build out their senior leadership teams. Jennifer is seen as a trusted advisor, with an expertise that allows her to guide clients through the lifecycle of their talent needs. This includes compensation design, performance management, market mapping, as well as other more highly specialized services in M&A talent mapping and executive communications. In addition to her deep relationship with her entrepreneurial clients, Jennifer is connected both regionally and nationally with senior leadership candidates as well as with a network of professionals in private company leadership and governance. She is also the Founder and Chair of Canada’s Best Private Boards, a first-of-its-kind national and annual program that recognizes the impact of governance on the performance of private companies.
About MondouxRollins Partners Inc.:
MondouxRollins Partners Inc., is an executive search and human capital advisory firm. We are a group of specialists, equipped with decades of experience providing talent solutions for private companies. We are risk-mitigators, trusted advisors and relationship-builders, and we are your one-stop-shop through the entire talent lifecycle - for your team, or for your board. We are also the founders of the Canada’s Best Private Boards program, a first-of-its kind national and annual awards program that recognizes the impact of governance on the performance of private companies.
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