Have Hard Conversations Before They Get Harder
Build a team that raises issues early and settles them directly.
Mid-year reviews are where a lot of unspoken feedback finally gets said. A deadline that slipped in February, a client update that missed the mark in March, a habit that has been slowing the team down since the start of the year: each was a short conversation at the time. Saved for the review, each becomes a harder one, delivered all at once to someone who has had no chance to act on it. Most of what makes a review difficult is the feedback that was held back for it.
Difficult conversations get easier and more useful the earlier and more often they happen. A leader who raises an issue while it is still small gives the other person time to fix it and spends ten minutes on a conversation that would otherwise take an hour. A leader who makes those conversations a normal part of how the team works gets something more valuable still: a team that raises problems with each other directly and treats honest feedback as part of doing good work together.
Having these conversations well is one of the most practical skills a rising leader can build. It shapes how fast the people you lead develop, how much of your time goes to problems that could have been solved weeks earlier, and how senior leaders judge your ability to run a team.
Raise the Issue While It Is Still Small
Most difficult conversations are delayed for kind reasons. A leader wants to give someone time to find their footing, waits to see whether a problem repeats, or saves the point for a better moment. The better moment rarely arrives, and every week of waiting makes the conversation larger. A single late report becomes a pattern, the pattern becomes part of how others see the person, and by the time the leader raises it, they are describing months of work instead of one piece of it.
Raise an issue the first time you are confident it matters, while it still concerns a single piece of work. At that size the conversation can be short and matter-of-fact: what you saw, why it matters, and what you expect next time. Ahead of mid-year reviews, read through what you plan to write about each person and mark anything they would be hearing for the first time. Feedback that would be news in a review is feedback the person needed months earlier. Have those conversations before the review, so the review can describe progress the person has already started making.
“Feedback that would be news in a review is feedback the person needed months earlier.”
Decide What Should Be Different Afterward
Before the conversation, settle on the one change you want it to produce. Leaders who skip this step tend to raise everything that has been bothering them, and the person leaves with a list of concerns and no clear idea where to start. A conversation built around one change gives the person something specific to act on and gives you both a clear way to see whether it worked.
Then gather the specifics that support it. Two or three concrete examples, each with what happened and the effect it had, do more than any general description of the problem. Specifics keep the conversation on the work, and they are far harder to dispute than an impression.
Finally, be ready to describe what good looks like. Many performance problems trace back to a standard that was never made clear, and the most useful part of a difficult conversation is often a precise description of the result you expect. If you find you cannot describe it, the conversation you need may be about the expectation itself, and part of the responsibility for the problem is yours.
Say It Plainly and Then Listen
Open with the point. Leaders often soften a difficult message by surrounding it with praise or easing into it slowly, and the person spends the conversation waiting to learn why they are there. Stating the issue clearly in the first minute respects their time and their ability to hear it. Kindness comes through in your tone and in a clear interest in their success.
Then ask for their view and hear all of it. There is often context you do not have: a competing priority from another leader, an instruction that was unclear, a process that is getting in the way. Ask what they would do differently, and work out the fix together, starting from their ideas.
Expect some resistance, and treat it as a normal part of the conversation. Some people dispute what happened, and the specifics you gathered let you stay calm and return to the facts. Others go quiet or agree too quickly, which usually means they need time to think. Offering to pick the conversation up the next day often leads to a more honest second conversation than pressing for agreement in the first.
Agree on the Next Step and Let the Issue Go
End every difficult conversation with an agreed next step: what will change, by when, and how you will both know. Follow up with a short written note of what was agreed, and set a check-in close enough that the person can show progress while the conversation is still fresh.
Once the conversation is over, judge the person on their next piece of work, and avoid reopening the issue each time you meet. Keep the details between the two of you. When the specifics of a hard conversation travel, the person loses trust in the process, and everyone who hears about it learns to keep their own concerns to themselves. If the agreed change happens, say so plainly and specifically. That closes the loop.
I once helped a leader whose performance was lagging turn it around, and three years later that leader was promoted. The path to that promotion started with a difficult conversation.
Give Feedback on the Choices Behind the Work
The hardest conversations to have are about judgment. Errors in the work are easy to point to, while a choice about what to prioritize, what to recommend to a client, or when to escalate a problem is harder to discuss, because it concerns how someone thinks. Leaders tend to put these conversations off the longest, and they often do the most for a person’s development.
AI is making them more important. As AI produces more of the first drafts, analysis, and recommendations a team works from, more of the work that remains with people is the judgment around it: what to ask for, what to keep, what to question, and what is ready to send to a client. When something goes wrong, the cause is increasingly a call someone made about the work. Leaders who can talk through those calls openly develop people whose judgment improves with every project.
Have these conversations by walking through the decision together. Ask what the person knew at the time, which options they weighed, and what they would weigh differently now. Then share how you would have approached it and why. Done regularly, this is one of the fastest ways to pass on judgment that took you years to build.
These conversations matter at every level, including with leaders more senior than you. I once helped a senior leader understand a bias in how they rewarded variable pay, a pattern that is easy to miss from inside the decisions and hard to raise with the person making them.
Make Hard Conversations Part of How Your Team Works
A team where difficult conversations are welcome is built through routine. Feedback that only arrives in formal reviews or after something goes wrong carries weight every time it appears. When it comes up whenever the team looks back at its work, it becomes ordinary. After a major deliverable, a client meeting, or a pitch, spend fifteen minutes on what worked and what should change next time, and begin with your own part in it.
Encourage the people on your team to raise issues with each other directly before they bring them to you. When someone comes to you about a colleague, ask whether they have spoken with that colleague first, and help them prepare for the conversation if they have not. Over time the team settles most problems among themselves, and the issues that reach you are the ones that need you. When someone on the team challenges one of your plans and turns out to be right, say so in front of the team and change the plan. Each time people see a hard point lead to a better result, the next one gets raised sooner.
People often come to me for advice on a difficult situation with a colleague. The first thing I ask is whether they have raised it with that person directly, and the answer is frequently no.
Have the Conversation Before the Review
Most leaders already know which conversation they have been avoiding, and mid-year reviews give it a natural deadline. Those reviews often feed decisions about pay and bonuses as well, and some of the most important difficult conversations concern how people are paid and rewarded. Over my career, I have helped correct a number of salaries so that women on my teams were paid on par with male colleagues in similar roles. None of those conversations were easy, and each was the right thing to do. Every leader has a span of control where conversations like these are theirs to have, and an organization gets stronger with every leader who has them.
About John Fildes
I grow the top line by connecting marketing to business strategy. By leveraging powerful positioning, content marketing, and client insights, I help organizations drive qualitative and quantitative results at scale.
I've built an amazing network of incredibly talented people over the years. What I've appreciated most is those who have invested in me, mentored me, and helped me become the talented professional I am today. I pay it forward by doing the same for other high performing professionals and entrepreneurs.
Learn More: Growth Leader | Business Builder | Leadership Multiplier
All views are my own and not those of my current or prior employers.
