Solution Saturday: Direct Reports Don’t Open Up

Dear Dan,

I work for a company that believes developing people is central to success. 

Part of my job is connecting with my direct reports in such a way that they feel free to discuss and address areas where they can improve. The trouble is, I have a direct report who clams up.

I feel the barriers go up every time I ask a question about her performance or aspirations. A conversation with her is like pulling teeth. She always seems protective. If there is an issue, it’s other people’s fault.

How can I get my direct report to open up?

Thank you for any suggestions,

Pulling Teeth*

after defining the problem draw a picture of the future

Dear Pulling,

This morning I imagined what it might be like to have a boss who expected me to be vulnerable and transparent. Frankly, it felt scary. I’m pretty open, but I can imagine how some people would be uncomfortable.

Having said that, vulnerability and transparency are essential to development. Fake relationships are all about maintaining the status quo and protecting ego.

Be aware that transparency and vulnerability are unusual expectations. Typically, in organizational life, we’re expected to have it all together. Vulnerability isn’t at the top of the list of desired qualities.

When someone is uncomfortable, treat them gently, not aggressively. Pull back when they pull back. Give them space. I’m not suggesting you avoid important issues. Just address them kindly.

How are you being vulnerable and transparent? Model the behaviors you desire. Just be aware that vulnerability and transparency may be off putting to some people. You might try telling a story of one of your failures. Talk about what you learned.

Allow for awkward silence in your conversations. Filling the silence prevents you from getting where you want to go. If the silence seems too uncomfortable, say something like, “I see you don’t have much to say, would you like some time to think about it?” Perhaps a brief postponement would be useful, as long as you come back to the topic later.

How might you prepare your direct report for the conversation? Perhaps you could send her an email with two or three of the questions you intend to ask. I realize this might send her into “report” mode. If it doesn’t work, try something else.

Get out of the office for a meeting. Try a coffee shop or lunch. Just be aware that this suggestion might make her even more uncomfortable. On this note, if you happen to travel together, use car-time to discuss light topics like hobbies, sports, current events, or the last vacation.

Don’t shy away from tough questions or uncomfortable topics. When you bring them up, do it with kindness. You might discuss your discomfort with how your conversations are going. Whenever you do this, avoid the trap of focusing on the past.

Explain your hopes for yourself. “I want to develop my ability to bring out the best in people. I’m not sure I’m doing very well in our conversations.”

Invite specific feedback on your performance from direct reports. “What one thing could I do to be a better communicator?” Dig into the topic. Look for specific, actionable behaviors.

When you receive generalities, say, “Thank you for that, but I’m looking for something that I can put into practice today.”

Adopt new behaviors. Discuss results. Adapt. (Model transparency and vulnerability.)

Give it time. Some people are naturally skeptical. They need time to see if you’re trustworthy. If time doesn’t help, discuss the advantages and disadvantages of skepticism. 

Understand the difference between friendship and partnership. You want direct reports to believe you’re on their team. You don’t want them to feel pressured to be your BFF.

Lastly, you might consider a 360 degree assessment that focuses on the skills required to create safe challenging environments. Maybe you don’t know what it’s like to sit across the table from you. I like narrative 360’s that are based on conversations, rather than surveys.

How might leaders help direct reports practice vulnerability and transparency?

*This question is the composite of two questions that two leaders recently brought up.

Queens Young Leaders - Cambridge University