May, 2026 | Article

Author Sandra Bekhor, MBA, CPQC,

Giving feedback is stressful for everyone – avoiders to straight shooters. Does any of this look familiar?

Sara was just promoted and is now managing her old law school friend. But Lisa is missing the big picture on her files. Sara needs to say something, but she’s afraid of damaging the friendship.
Luke knows he’s very direct. He’s fast and efficient. He says exactly what he thinks in the moment. So why don’t they get better, even when he tells them exactly what to do?
Tom assigns what he needs to, and when it comes back with errors (the same ones, again and again), he just fixes them. That’s his job as the senior lawyer, isn’t it? Besides, he gets along with everyone and he likes it that way.

So, what’s this aversion really about? Managers worry they’ll appear unfair or trigger a negative reaction, so they delay, delegate, or dilute their feedback. Meanwhile, issues quietly fester, underperformance gets entrenched, and high performers get ignored because “they’re fine”—until they leave for somewhere they can really grow.

At some firms there’s an expectation that HR can “handle” performance‑management conversations on behalf of lawyers and that this checks the box. But associates want to hear from the people who assign them work, see their day‑to‑day performance, and understand as lawyers what “good” looks like. When HR is asked to step in, it weakens the sense of being known and supported by the person whose opinion matters most about their future.

Underneath much of this discomfort is social uncertainty: it’s not clear what “appropriate” looks like in this kind of conversation, especially when you’d really like to avoid creating tension with someone you work with every day.

Here’s where HR can help. Instead of asking managers to “be braver” or “just do it,” you can give them a simple, shared structure to lean on. It’s not unlike having court rules. Even very polite lawyers can shift into fierce, focused advocacy in the courtroom because there’s a structure that makes that behaviour permissible, expected even.

Giving feedback in 3 stages

Before: getting ready

• Get clear on goals: what success looks like in this role, for this person’s career, and for the firm.
• Choose 1–3 priorities for this conversation rather than “everything at once.”
• Gather concrete examples (good or bad) so you’re talking about real data, not impressions.
• Check assumptions and biases, including any recent events that might colour your view.

During: the conversation itself

• Manage yourself immediately before and throughout the meeting. Notice any signs of discomfort – sweaty palms, fidgeting, shallow breathing. Take a few mindful breaths to come back to your calm, grounded self.
• Make it a two‑way conversation. Ask questions, stay curious, and resist the pull to assume you already know the whole story.
• When appropriate, share a story from your own experience to show you recognise the hurdles they’re facing. This helps build trust and makes it more likely they’ll respond and your conversation will have real impact.

After: turning it into a rhythm

• Agree on 1–2 concrete next steps to establish accountability.
• Set a schedule for ongoing feedback conversations, so you’re not waiting for a crisis or an annual review.
• Ask for feedback on your feedback, and make it easy for them to be honest by sharing how their input will help you support them better.

Hybrid work amplifies all of this discomfort. Thank‑yous get shortened or forgotten. Small issues are harder to see until they’re big. And because people aren’t chatting casually, giving feedback feels even more socially awkward.

To get comfortable with this process, we need to take a closer look at what it means to be “kind.” Avoiding hard truths or just “being nice” can feel kinder in the moment. But it’s not kinder to let someone believe they’re performing at a higher level than they are, only to be deeply disappointed when a promotion doesn’t come through.

We also need to look at what it means to lead. Hierarchy isn’t always helpful. The team needs to know that you’ve been there yourself and can still relate to what’s going on for them—as an ally, rather than a distant superior. Being willing to be a bit vulnerable and share something relatable from your own journey helps people see that they’re not being judged for talking about current limitations or struggles.

I can’t count the number of times I’ve coached smart, young professionals who share a real struggle and, when I ask if they’ve told their supervisor, the answer is no. Every time. Why? Because they worry it will make them look bad and be held against them later. It doesn’t occur to them that by asking for help they could get the support they need and possibly accelerate their growth as a result.

At the end of the day, this process is about building trust. Being honest isn’t always easy. Adjusting your communication style so you can be heard—and so you can really understand—isn’t easy either. But if you trust someone enough to be genuinely honest with them about how they’re doing and what they need to do to get better, they may trust you enough to be honest about what they really need.

You can be that manager who makes your team feel safe enough to open up—and model the way for your leadership group to follow.

That’s what will make your keepers want to stay.

Sandra Bekhor, MBA, CPQC, is a practice management coach and Certified Positive Intelligence Coach at Bekhor Management. For 20 years, she has supported lawyers and other professionals in building practices that align with their real goals. Sandra presents extensively for professional bodies, including for TLOMA, the Toronto Lawyers Association, and the Canadian Bar Association, and hosts the ‘Get in the Driver’s Seat’ podcast on leadership in professional practice.

To learn more:
https://www.bekhor.ca/
https://www.youtube.com/@BekhorManagementToronto
https://www.linkedin.com/in/torontomarketingconsultant/
https://GetInTheDriversSeat.buzzsprout.com