How Great Bosses Get Honest Info

When you’re the boss, effective communication with your team can be especially fraught. We all know the difficulties team members have telling their manager bad news or disagreeing with a senior executive at their company, even when it’s an important message the leader should hear.

The research on how power affects the willingness of those without much of it to speak up and disagree with or challenge those in charge is well known. People keep their mouths shut and even publicly agree with their boss in meetings, despite not agreeing with their boss or knowing that they’re wrong. This is so common that there’s something like a journalistic cottage industry in giving advice for how to tell your boss what they need to hear (without getting fired).  

Why does such a well-known organizational challenge remain so pervasive? Because those in charge believe it when their team agrees with them. Executives like it when their team agrees with them. Leaders like their own ideas (don’t we all?), and bosses send all sorts of signals to their team that agreeing with them gets rewarded. Think about the leaders you know. Do most of them surround themselves with people who think like them or with people who think differently and challenge them regularly?

This came up recently in my work with Brad—the newly appointed COO of his company—who is making truly transformational change across his organization. While working with his team on new strategies, he has become increasingly uncomfortable as he’s realized that almost anything he says goes. He’s begun to recognize the challenge associated with his recent promotion: he feels cut off from facts and further from the truth. He knows that in his new role he is more dependent on his team for information than ever. He isn’t a leader who feels that he has all of the good ideas, and yet he has found just pushing his team to be more outspoken and challenging hasn’t worked.

As we discussed his dilemma I was reminded of Janet, another leader with whom I worked, and how she faced down this inevitable difficulty of leadership. Janet was particularly adept at managing this struggle. She ran an industry-leading company and was a powerhouse of a problem solver. Like Brad, she realized that sitting in her corner office, she was cut off from the information she needed to be an effective leader. She had to rely on her team who she knew would have a tough time being straight with her even though she trusted them. She better understood the challenges of being straight with your boss than most of the other leaders with whom I’ve worked. After all, she hadn’t always been the boss. Before she was CEO, she remembered confronting the same dilemma that her staff now faced.

Janet recognized that the information flow wasn’t poor because her team didn’t want her to have the best information. It was because, among other reasons, Janet was generally acknowledged to be the smartest person at the company, and so she could be unintentionally intimidating. Plus, there are times where people don’t want to be completely open because that story may not benefit their budget or their part of the business. But Janet knew that most of people’s reluctance to disagree with her, push an agenda she might not immediately support or say what needed to be said wasn’t their conscious desire to deceive her. The situational demands of an organization tend to bend people’s perspectives to what they believe the boss thinks or wants. She hated that and did what she could to manage it the best she could, knowing there is only so much a manager can do to fight this bit of psychology.

This was important, so as I worked with Janet I got to observe her tool kit for getting the frankest dialogues from those with whom she worked. What I noticed was that over time she sharpened her technique for making the playing field feel more even.

Specifically, when she was really interested in what someone thought she hid her perspective. She did this by being quiet early in conversations. I remember helping to facilitate a meeting with her team soon after she became CEO, and at the end of day one, a member of her team pulled me aside and said that Janet needed to speak more, she was the CEO now. But that wasn’t Janet’s way, especially early in a conversation. She tended to speak more as the conversation progressed, especially in group meetings as she got a feel for people’s points of view.

Janet was also known for asking questions more than sharing her perspective. These questions didn’t always make people comfortable because they wanted to know what the boss thought, but it was her technique for developing her own perspective from unbiased information (or at least as unbiased as she could get).

When team members let her know that they really wanted to know what she thought, she was transparent about how she worked on problems and how gathering the best information possible was important to her. In her one-on-one meetings with her staff, she would tell them how she had come to learn that for many, her role caused people to avoid disagreeing with her.

Janet had a great story about how she didn’t like a particular word; it was business jargony and had become somewhat meaningless. Her head of HR went around the company telling people never to use the word in her presence, in spite of the fact that it’s one of those terms that’s common in any big company. 

In all of these ways, Janet did her best with one of the most insidious challenges of leading a company but felt that it only worked some of the time. Still, Janet’s efforts created a valuable starting point and one that has helped Brad really evaluate what his team thinks and feels about the transformation he’s leading at his company.

When leaders ignore the effect that their role has on people’s willingness to tell them the truth, they can expect problems to arise. Some of these problems will be cultural and others more performance-oriented. When unexpected problems arise and leaders find out that the surprise was not unexpected for everyone, it is one of those proof points that some cultural norms are not serving your business. In such situations, finding out that some people in the business knew there were issues that weren’t being dealt with or elevated should be a sign that the company’s leaders could relate differently to encourage the openness and psychological safety that are the hallmarks of great companies.