Here’s a situation that no one wants to be in. Let’s say you report to the founder/CEO of a startup. The founder has no management experience and the startup has grown beyond a size they can comfortably control through personal intervention. Because of your functional and interpersonal skills, it has become your job to run interference between the founder and everyone else.
One of my clients, who’s in that exact situation—we’ll call him Steve—called me last week to vent and get advice. He described a work environment that borders on toxic—and several team members are so fed up with the founder’s unhelpful behavior and communication that they’ve become flight risks.
Steve emphasized that this founder—we’ll call him Mitch—isn’t someone who enjoys treating people horribly. But he is so anxious, fearful, and poorly regulated that he acts unprofessionally, which unfortunately creates the same kind of negative work environment that would occur if he mistreated people intentionally. Mitch expresses his distress and frustrations in ways that are overly critical and therefore hurtful to his colleagues, which is not only upsetting, but disrupts their focus and ability to get the job done.
First, Get Your Boss’s Buy-in for a Heart-to-Heart
Steve and I discussed how to navigate a difficult conversation with Mitch, with the intention that Mitch hear and accept the input and observations. Steve acknowledged that Mitch was already aware that he gives feedback poorly, particularly when he’s stressed and overwhelmed, and that the rest of the team actually functions better when he’s not personally involved—and that these were the reasons why he had promoted Steve to coordinate with the other employees, essentially acting as a buffer.
Still, Steve worried that reminding Mitch about his commitment to stay out of the day-to-day and not critique staff directly would cause Mitch to become defensive and combative. So our first focus was on getting Mitch’s explicit or tacit permission to provide feedback. We discussed how to open the conversation in a way that would support Mitch’s concerns and not feel like an attack. Steve decided to say something like: “I know you’re very concerned about our productivity right now, and I have some ideas about how we could improve our performance.” The goal was to show Mitch that Steve could help the organization attain a brighter future if Mitch would follow Steve’s recommendations.
Gear Your Comments to Your Boss’s Likely Responses
We brainstormed improvements in sales and internal production that Steve was confident Mitch would agree were valuable. The next step was for Steve to share just a few of his observations of things that needed to change, providing specific examples that would be compelling to Mitch. Steve planned to describe briefly a recent time when Mitch’s reaction to a problem had been so out-of-proportion that employees considered quitting because they believed Mitch hated them and considered them worthless.
I reassured Steve that he did not have to delve into why Mitch was anxious or act like Mitch’s therapist—all he had to do was describe the more productive behavior that he needed from Mitch and then give Mitch the chance to see that Steve could be relied on to support that behavior.
Combine Feedback and Support
When you explain a desired behavior change to a subordinate employee, you might say, “I see that thus-and-so was tricky for you, so I’m going to partner with you on it to give you practice in the new way.” Or even: “Last week didn’t go so well, so this week I’m going to assign you function Y rather than function X.” But with a boss, especially one like Mitch, it’s important to make the point that his behavior is powerful enough to have a positive or negative impact on everyone, so that whenever he gets overinvolved and overly upset, it’s damaging to the organization.
Together, Steve and I drafted language that would demonstrate a stance of compassionate validation toward Mitch. Steve would explain how Mitch did not need to be personally involved in every problem he saw, and how, whenever Mitch worked himself up excessively over end-of-month activities, he actually prevented himself from starting off the new month on the right foot—so it was no wonder that Mitch was always frustrated and on the verge of blowing up!
I advised Steve that if the feedback session was going reasonably well at this point, it would be a good time to pause the conversation and ask Mitch explicitly how things felt to him. Then, to ensure that Mitch wouldn’t feel too pressured, Steve could offer to check back in a day or two to confirm how they would go forward together, tweaking the plan if necessary, and meanwhile continuing to offer Mitch views of a brighter future.
Be Prepared for Reversion to Old Behavior Patterns
Steve later reported back that the conversation went very well. I reminded him that this did not mean the challenges were over. I advised him to be ready for Mitch to forget his pledge to behave differently and to get overly involved occasionally—but then Steve could kindly disentangle him once again.
Here’s a brief summary of the steps we structured for the conversation:
- Acknowledge your boss’s overarching concerns.
- List the better outcomes that could result from the changes you’re about to propose; share the idea of the brighter future.
- Explain what you’ve observed that doesn’t work with just enough detail for your boss to know what you’re talking about, but not in so much detail that they get caught up in the story.
- Propose the behaviors you want to see.
- Reiterate how that behavior will help bring about a brighter future.
- Check explicitly for your boss’s reactions.
- Expect to go back and do all this again.
Onward and upward—