How to challenge without sounding critical
- mayadolgin
- 1 day ago
- 3 min read
(April 21, 2026 Newsletter)
It’s a fine line – and one that many people get wrong. Something is being done incorrectly, isn’t being carried out as you want, that someone misunderstood your instructions or even purposely disregarded them.
The person matters to you, either out of a personal affinity for them or because you just recognize that their success is your success.
How can you find the words to challenge them without being overly critical?
Why it matters
This is a classic “both and” situation. Many people think that you have to either prioritize the relationship or the outcome, but they’re wrong (luckily).
Skilled leaders can challenge the situation without attacking the person.
If you want your company to move at lightning speed, you have to cultivate an environment that encourages learning – which cannot happen under excessive and prolonged stress.
That means training your managers to be top notch coaches and this skill is a key one for them all (and you) to develop.
5 practices of skilled challenges
Watch out for blame. Let’s be honest – it’s very likely that your first reaction will involve blaming the person. That means you’re human. The difference, though, between being a human and being a leader is your second reaction. Bad leaders blame. Good leaders blame, then share responsibility. Great leaders experience the first (to themselves!) and pivot seamlessly to a forward-looking, collaborative stance. This means staying focused on the issue and not the person.
Focus on outcomes. What do you want? Keep the conversation focused on the goal you’re working toward, not the problem you’re trying to fix. This doesn’t mean ignoring the gap between here and there, rather keeping your eyes (and theirs) on the prize. This will keep motivation up and the blood pressure down.
Use “we” wisely. There’s a tricky balance between wanting to indicate that you’re part of the same team and losing sight of who’s responsible for what. Use this as a guide: We want the same successful outcome, but we aren’t working on the same parts of the project.
Support solutioning. The main question is “What else do you need to succeed here?” No lobbing the hot potato at them and walking away. Support can mean different things to different people, ranging from brainstorming solutions with them, inviting them to share an earlier draft of the next version, or connecting them to a colleague who can be a resource to make sure the next version that gets to you is closer to your vision. It can also mean adjusting timelines or reassessing other workloads to free up their time.
End with encouragement. If you’ve been harsh in the conversation – even if focused on the content and not the person – it’s still best to end with a “here’s why I believe in you” statement.
Final thought: You won’t get it right every time, which will largely depend on the inner work you can do to close the gap between your first and second reaction. Performative attempts are easily perceived through body language and tone, so don’t skip the work to get Above the Line.
The Coaching Corner
An easy formula to acknowledge before asking
One of the things I encourage my clients to do when they’re leaders learning to develop a coaching stance at work is to avoid peppering their team member with questions. While the intention might be “coaches ask good questions,” it can come across as an interrogation if you never stop to acknowledge, validate, or check for understanding.
Here’s a simple two-step formula you can start using today:
“I’m hearing X. I’m wondering Y.”
“I’m hearing you say that this project is turning out to be more complicated that you expected. I’m wondering what sort of support you want from me to solve that.”
Or in other words: “It sounds like this project is turning out to be more complicated than expected. What kind of support can I give as you solve for that?”
Recommendations
Growth mindset vs. fixed mindset – I watched many videos looking for one that explains the topic well, so you wouldn’t have to.
“The shadow in the system” – Another article about the complexities of team dynamics, a topic of increasing interest to me as I take on more and more team coaching projects.
“The Power of Options” – I’ve sent this out before, but shared it with a client today and was reminded how much I love the idea of expanding our comfort in the four stances discussed.
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