Jill Geisler: How to give feedback to your boss

May 31, 2024 11:41 am

It was a wonderful event. The executive who promoted me and other women into management when it was still a rarity (this was the early ‘80s) was receiving an award for his efforts. In his acceptance, he told the audience, “You’re honoring me for being selfish. I want only the best people on my team, and I hire accordingly.”

My fellow female colleagues and I were so darn proud to work for him. And I was struck by the authority and authenticity he brought to his speech that night. The next day at work, I decided I should tell him that.

When I entered his office, I felt uncomfortable. I was just a rookie manager, and he was a veteran leader. Who was I to tell him what a fine job he did? He must know that. I stumbled through my words of praise. Until he stepped in to save me.

“Why, thank you,” he said. He then told me that when you get into the top office, you don’t usually hear feedback like that. You hear about problems that need solving. He said it was a great change of pace to hear someone tell him he’d done something well.

Leaders need love, too

His message has stayed with me for decades. The higher you get in an organization, the less likely you are to hear precisely what you’re doing well. Flattery from obvious sycophants aside, leaders know that genuine, specific feedback about their strengths and successes don’t always come from their direct reports.

That’s why I encourage people to learn how to provide genuinely helpful feedback of all kinds to their leaders. If they lead effective meetings, tell them why it makes a difference. If they inspire with their pep talks, tell them how it inspired you. If they teach or coach well, share the impact they’ve had. If they admit mistakes, tell them how much you admire them for it. And if, like my early boss, they’re determined to make the workplace more diverse, let them know how much it matters to you and to the quality of the workplace.

6 things to consider when wanting to share constructive feedback

But what if your manager has some weaknesses, blind spots or has blundered? I’m not talking about toxic bosses, I’m talking about everyday leaders who aren’t perfect (no one is) and who would benefit from knowing the impact their gaps are having on the workplace, the workers or the work.

How do you find the right way to share criticism with the person who evaluates your performance or signs your paycheck? You do it with care, of course. And following are some of the things to care about.

  1. What pressure is your boss under right now? Could your boss’s actions be related to something that’s out of their control — like marching orders from above? It can help you frame your approach. “Could I talk with you about the hiring freeze? It may be written in stone, and if so, let me know. But if not, you may recall you gave me permission to fill our opening, and we were about to make an offer. Is there a chance we can slide this one in?”
  2. What’s your boss’s leadership style? Is it formal? Informal? Top down? Collaborative? If your boss is buttoned-down, you may want to make your approach more formal and be prepared with some data to back up your words. “In the all-staff meeting, you said that we have a widespread problem of excessive overtime. My group has worked so hard on efficiencies. As you can see from this report, we eliminated overtime in this quarter. They and I are hoping that you know that.”
  3. How’s your timing? Some bosses don’t mind being challenged in a meeting. Others may feel it’s an intentional public undercutting of their authority. Ask yourself: “Where will my negative feedback be better received — in front of a group or one on one?” For one of my bosses, I knew that one on one was best. I’d often say, “I don’t think you’d respect me if I had a concern and didn’t have the guts to tell you personally about it.” He seemed much more disposed to respond positively when I delivered it that way.
  4. Who are your allies? When issues affect multiple people, it can help to speak together. Two of you, especially two of you who are high performers, may ask for a quick check-in with the boss. “We wanted to ask if we could get those biweekly stand-up meetings back to regularity. We know you’ve had to cancel a few, but the group really benefits from hearing from you.”
  5. How sensitive is it? What if you are having problems with a colleague your boss has hired or clearly admires. You’ve tried to address it with the individual, to no avail. You need support from your boss to get things resolved. Go to your boss with a request and a plan. “I’d like your guidance. Despite several conversations, I’m not getting the information I need from Pat in accounting. I’m planning to try again but will be more direct this time about how the delays are hurting us. You know Pat pretty well. Do you have any advice for me?” Getting the boss invested on the front end can help you get a successful outcome.
  6. What delivery method are you using? The more important or serious the issue, the more important it is to share your message in person. Your boss may prefer to communicate by email, but try to get a meeting. Email lacks tone, and even the most carefully worded message could come across as a demand instead of a request or as an attack instead of an alert. If your boss insists on getting something in writing, read it out loud before you send it. Imagine you’re the boss. Could it sound overly aggressive? Whiny? Disrespectful? (As in, how could you, the boss, let this happen?) Is it clear? Even if it reads perfectly, do your best to schedule a meeting to discuss what you’ve written.

The bottom line

Whether you’re delivering positive or negative feedback to bosses, the angels are in the details. Don’t just tell them you admire or appreciate what they’ve done, tell them why it is meaningful. Don’t just tell them morale is down, describe what you’re seeing and how prevalent it is. And for good measure, offer a reasonable suggestion or two for a solution that you’ll gladly help with.

Remember what that long-ago leader taught me: The higher you go in the organization, the more isolated you can become from the very feedback you need.

Don’t assume that doesn’t describe your boss. Speak up. 


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