Most leaders say they want trust on their teams. They talk about it in meetings, put it in the values statement, and tell people the door is always open. And yet the team still goes quiet when it matters, the hard feedback never quite arrives, and small misunderstandings turn into fractures nobody saw coming. The word gets used a lot. What it looks like in practice is a different conversation.

Jen Wilson is an executive coach, leadership strategist, facilitator, and speaker. She works with senior women leaders, executives, and high-capacity women who are successful on paper but overextended behind the scenes, through her 90-Day Individual Edge Coaching Program and her corporate team coaching and training. Her work helps women and their teams stop being the default solution for everything and lead with clarity, authority, trust, and sustainable impact. Jen is also one of Amanda Kaufman's business besties, and she asked for this conversation to be real talk rather than "puffed shirt" leadership talk. On this episode of The Amanda Kaufman Show, Jen breaks down what trust actually requires, the single question she has seen transform teams, and the reason so many capable people get promoted into leadership without anyone showing them how to lead.

Trust Is the Foundation of Leadership

Trust sits underneath everything else in leadership, and it grows from directness that does not have to be harsh. Jen describes this as real talk: being direct and candid while staying kind.

How It Matters: Jen points out that trust is a word people use constantly in corporate speak, and the interesting part starts when someone slows down to ask what it looks like in practice. A team can only begin decoding the real issues once people feel trust, and connection travels with it.

How to Do It: Speak plainly and stay compassionate at the same time. Amanda describes Jen as a gorgeous mix of no BS and deep kindness, and that balance is the model. Jen notes that women leaders in particular have often seen models of directness that look harsh and mean, and that version is not the goal.

Common Mistake: Treating candor and kindness as opposites. Most leaders who have only seen the harsh version of directness either avoid it entirely or copy it. Neither builds the kind of trust that lets a team talk about what is really going on.

Trust Starts With Reading Your Own Reality

Building trust begins with three capacities: reading your own reality, reflecting on it, and investigating with genuine curiosity. Jen learned this from an engagement where she was brought in to light a fire under an executive team.

How It Matters: Before doing that, Jen stepped back to look at the leadership. In one-on-one conversations with each executive, she found that what one person saw as mistrust in a leader looked completely different to someone else. Those differing views of trust rippled throughout the organization, and fractures started to happen.

How to Do It: First, slow down enough to interrogate reality for yourself instead of accepting what comes through the virtual watercooler about this boss or that boss. Second, take time to reflect on your own lived experiences, because, as Jen always says, all conversations are with ourselves and sometimes with other people. Third, stay in a mode of curiosity and ask questions that truly investigate.

Common Mistake: Skipping straight to conclusions. Most people form an opinion of a leader, or a team member, from secondhand impressions and their own internal analysis. Trust gets built at the foundational level only when someone takes the time to check.

Leading in a Learning Mode Requires Detachment

Leaders who keep growing are willing to detach from the way they have always done things. Jen calls this operating in a learning mode, and it takes a little humility.

How It Matters: Jen was a leader inside an organization for almost 18 years. Looking back, she can see how attached she became to her own ways of working. She tells the story of a report she started when she first joined, how she freaked out when they changed its colors, and how she was still producing it 18 years later. A lot of times what gets someone to where they are is not the thing that will get them to the next level.

How to Do It: Interrogate the reality of your own leadership, especially because leadership is a perceived position of power, even though everyone on a team holds some level of power. Be willing to say, "Actually, I don't know everything."

Common Mistake: Blaming the change on the people coming in. Jen remembers being in a leadership position when millennials hit the workforce, and admits her generation of leaders was not ready. Most leaders find it easier to say "it's a new generation" than to look at their own attachment to old methods.

"What Am I Missing?" Is the One Question That Builds Trust

The leaders Jen has seen truly hear from their teams ask one question at the end of presenting anything: "What am I missing?" She has watched that question transform teams and the way they operate together.

How It Matters: A lot of leaders tell Jen they have an open door policy. For her, that is something to interrogate, because most team members do not want to walk through an open door. They often leave with more work, or the trust simply is not there. The question "What am I missing?" starts from a different position: I know I'm missing something.

How to Do It: Build the question into the end of every presentation, proposal, or plan. Here's the idea, now what am I missing in this idea? Jen is clear that it requires more than the question alone and is never a one and done. It works best alongside other tools a leader practices over time.

Common Mistake: Assuming availability equals trust. Amanda's take on the open door policy: what does that even mean, and how does anyone know access was the problem in the first place? Most leaders announce the policy and never check whether anyone uses it.

Leadership Works Best as a Relationship

Leadership falls flat when it becomes a box to check. Amanda sees a pattern, especially with new leaders, of trying to make leadership transactional.

How It Matters: Amanda compares "call me anytime" to a real relationship. People who respect each other's time book a meeting so they can be proactive about connecting. Treating leadership as a checklist misses the forest for the trees: the reason the role exists, how well the leader advocates for it, and how well they understand the way people connect with each other.

How to Do It: Start from the purpose of the role. Jen sees the same story over and over: a technical expert does amazing work as an individual contributor, gets promoted, and now leads a team. When they reach her, they almost always say some form of "No one ever told me how to do this." Naming that gap is the first step to filling it.

Common Mistake: Expecting the organization to hand over the roadmap. Amanda shares that in corporate America she assumed a structured environment would give her everything she needed to reach the next level, and she was not really connecting with what that next level would require. Asking her boss felt too risky. Most high performers carry that same quiet assumption.

Coaching Helps Leaders Walk Through the Doors Already Open to Them

A coach helps a leader navigate the internal pieces that keep them from acting on the opportunities and advice they already have. Jen's own career is the example.

How It Matters: Jen had sponsors who were flinging doors open for her and walking her into boardrooms, and mentors who knew her industry and gave her great advice. She still did not walk through those doors or do what her mentors told her to do. It was only after working with an executive coach that she began to navigate the internal part of her that was holding her back.

How to Do It: Think of it as a triangle, the way Jen does. Sponsors open doors, mentors share what they know, and a coach is the third part that helps realign the compass so the leader actually walks through. That is the work she now does for high-performing women, so they can follow their mentors' guidance, challenge it, ask more powerful questions, and build a legacy that does the same for someone else.

Common Mistake: Relying on reading alone. Jen is a big believer in books, research, and models, and she is just as clear that theory and action have to go hand in hand. Reading about trust teaches little without practice in the day-to-day micro moments, and an eight-hour training cannot resolve a team's conflict on its own.

Conclusion

Jen Wilson's approach to trust comes back to a few connected practices. Lead with real talk that stays kind. Read your own reality, reflect on it, and investigate with curiosity before forming conclusions. Stay in a learning mode, even when the old way feels comfortable. Replace the open door policy with a question that assumes something is missing. Treat leadership as a relationship, and get the outside support that helps you walk through the doors already open to you.

The one question is simple enough to try in your very next meeting. Ask it, listen to what comes back, and keep asking.

To hear the full conversation with Jen Wilson, listen to Episode 379 of The Amanda Kaufman Show on YouTube, Apple Podcasts, or Spotify.

Frequently Asked Questions

What is the one question every leader should ask to build trust?

"What am I missing?" Jen Wilson has seen leaders who ask it at the end of presenting anything transform their teams and the way they work together. The question starts from the assumption that the leader is missing something, which invites people to speak up.

Does an open door policy build trust with a team?

Not on its own. Jen notes that most team members do not want to walk through an open door, often because they expect to leave with more work or the trust is not there yet. Asking a direct question like "What am I missing?" does more to bring people into the conversation.

How can a leader start building trust?

Start with three capacities Jen teaches: read your own reality, reflect on your own lived experiences, and investigate with genuine curiosity. That means slowing down instead of relying on secondhand impressions. Trust built this way rests on a foundation the whole team can stand on.

What does an executive coach add that mentors and sponsors do not?

A coach helps with the internal side of leadership. Jen had sponsors opening doors and mentors giving great advice, and she still did not walk through those doors until she worked with an executive coach. The coach helped her slow down, realign her compass, and act on what she already knew.

Where can I find Jen Wilson's free leadership resources?

Jen's free gift, 100 Must-Have Resources for Executives, is at https://jenrwilson.com/100-leaders. She calls it her Leadership Vault: 100 resources for leaders in a sortable Google Sheet, from two-minute reads to full books. You can also find Jen at https://www.jenrwilson.com and connect with her on LinkedIn at https://www.linkedin.com/in/jenrwilson/.