The Founder’s Paradox: How to Get People to Tell You What They Really Think When They Are Afraid To

founders paradox really think

“What do you think?” This can be one of the hardest questions to answer. Especially in an all-company meeting, when the person asking is the founder or CEO. Silence is understandable — people may feel timid, worried about saying the wrong thing and looking foolish in front of their colleagues and other leaders. So, you get blank stares and tight lips. You truly want to know the answer, but people seem afraid to speak up.

I have experienced this in different ways at different points in my career. Like most people, I have worked for tough managers — it was not always easy sharing what I thought was the truth earlier in my career. I have also had the opportunity to start or be an early employee of six cloud-based technology companies. The last two ventures were acquired by well-known public companies and I got to see how these challenges played out at a global scale.

As a founder, the paradox is always there and must be wrestled with at each stage of the company’s growth.

Now, receiving direct feedback is something I relish. And I can tell you that it is an important issue to address that feedback in a rapidly growing company like Aha! — we need everyone to be engaged and share their thoughts.

In six years, we have continually grown the business in a people-first way. We are the 13th fastest-growing private software company in the U.S. and have nearly 100 teammates distributed across the world. The team at Aha! comprises the most exceptional group of people I have ever worked with. But we are definitely not immune to this paradox.

The key is to balance being a strong leader with an awareness that your title might hold people back from expressing what they truly think — and as importantly, what they are feeling. Of course, this gets progressively harder the larger that your company gets.

If you are fortunate enough to rapidly grow your company, then you will start to feel the shift.

In the early days when a company is small, it is relatively easy to make strong connections. At this stage, you know everyone really well. You interact regularly with most folks and people really know what you are all about. It is easier to express your opinion in this kind of tight-knit environment.

Close relationships only thrive when you have time for frequent interactions. Yet as you grow, the number of people you interact with daily decreases. Not because you do not want to — but because it is simply impossible due to the demands on your time. Add to that the emergence of leaders within the organization, and you now have more leaders between you and the broader team.

I can tell you that the depth of the challenge is directly related to the level of your company’s success and the size of your team. But no team is too large to honor transparent feedback.

Here is what I have found helps to banish the silence and engage the team:

Make space
In many ways, sharing your thoughts takes work. Not speaking up is painless and poses few risks. So, respect each individual and know that feedback can actually be an indication of deeply caring about a mission, company, and team. As a leader, you have to explain that learning and improvement require transparency and conversation. Then, back it up — create opportunities to spark the conversations that need to be had.

Keep asking
When things are on track, it is fun to receive feedback. Everyone will share the positive. When things are not going as well… asking for those thoughts is not as appealing. Have the courage to ask in good and bad times. And keep asking. It does not have to be you solving the ups and downs either. When you do not have all the answers and need help from others, acknowledge it when you ask.

Accept answers
Our inclination as founders is to jump ahead to solving the problem or even to dismiss the feedback if it does not ring true to us. But a solution is not always possible or wanted. And being dismissive will get you nowhere. Listen deeply and accept the answer — especially if the conversation is about you. As a mostly rational thinker, this is another paradox I keep working at: The answer might not be true for you, but it is true for the other person.

Answer back
A meaningful dialogue requires at least two people to participate. Otherwise, you just have an echo chamber. While your position in the company gives you a certain level of prestige, that does not mean that you cannot engage with others directly. You always should listen first. But you have an obligation to respond with honesty if you expect others to do the same.

Be true
Share your core beliefs. Hopefully, you have already done this in a formal way and published a framework that is driven by your company’s values. This will help the team and it will help you. Because while you may not always agree with what people say, you should aim for understanding — while remaining true to your responsibilities to the entire team. And most importantly, you will need to make decisions based on your own principles and what you believe is right and true.

Everyone has their own leadership style and every company culture is unique.

But one thing most successful companies have is that they are open to feedback coming from every person on the team. If you are a founder who is passionate about building a lasting business, you will acknowledge that it is likely not easy for others to approach you. It is even harder for them to tell you what is really on their mind and in their heart.

Read more of The Founder’s Paradox.

About Brian and Aha!

Brian seeks business and wilderness adventure. He is the co-founder and CEO of Aha! — the world’s #1 roadmap software — and the author of the bestseller Lovability. Brian writes and speaks about product and company growth and the adventure of living a meaningful life.

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