Talking to Leaders: 5 Mistakes to Avoid When You Talk to Busy, Burdened People
Talking to leaders can be challenging under the best of circumstances. But, with a little planning, there are five mistakes you can avoid.
At one point in my career, I worked in downtown Chicago and commuted by train. Late in the day, every commuter is trying to wrap up and get out the door. You’re busy, you’re rushed, and the train isn’t going to wait. The pressure builds as the list gets longer.
Now imagine someone needs to talk to you in that moment.
At work, many of the leaders we most need to reach feel that way all day.
What is a busy, burdened leader?
A busy, burdened leader is someone who has more to do than time to do it and is under pressure to perform. It might be your boss, a customer, a partner. It could be you. In that mental state, people become scattered, irritable, quick to judge, and hard to read.
Put yourself in their head for a minute. There are deadlines and competing priorities. There are people hitting them up every minute. They’re running late and worried they’re missing something. They can’t zero in on what matters most because a million things are happening at once. They get mad when normally they wouldn’t.
Now think about how you would want people to talk to you on a day like that.
What are the five mistakes when talking to leaders?
If you’re trying to have a conversation with a leader, or any truly busy person, there are certain mistakes you must avoid at all costs. The mistakes usually come from ignoring five things: topic, time, timing, role, and response. Each is something you must address if you hope to get their attention.
- Topic: What are you talking about, and why should it matter to them?
- Time: How long is this going to take?
- Timing: Is this the right moment for this conversation?
- Role: What do you need from them?
- Response: Will you give the other person the chance to say something?
Making any one of these mistakes can hurt your working relationship. Frustration builds. The other person starts to lose trust and confidence in you, because each mistake undermines you as a communicator.
Why does the topic have to come first?
A person who is running late, busy, burdened, and buried wants you to get to the point immediately. Frame the topic right out of the gate: what you’re talking about, why it matters to them now, and what you’ll cover. As an example, during a recent stretch of competing deadlines, a meeting landed on my calendar with no agenda. I asked for one. None came, so I declined the meeting. When I’m that busy, I need to know exactly what we’re talking about before I give the time.
How much time should you ask for?
Tell people how much time you need, and always overestimate. I can’t count the times I’ve watched someone begin a conversation with no idea of how long it would take.
Here’s the problem. You need 15 minutes. I’m hoping for two minutes, because I’m not a mind reader and you didn’t tell me. As you burn through my time, I’m losing my mind, because I have other things to do.
“Do you have five minutes? This won’t take more than five” is far better than “Got a minute?” that turns into ten. Busy people don’t have long stretches of time, so be realistic and economical.

Hoping to talk to a busy person? Choose your moment, and be crystal clear on what you will say and what you need from the other person.
When is the right time to talk to a busy leader?
Timing is about choosing your moment. Before you begin, ask yourself:
- Are they at their best right now? I try to talk to people when their energy is high. That often means getting on their calendar first thing in the morning, or coming in a half hour early to do it.
- Are they about to run somewhere? Catching someone on the way into a meeting, onto a Zoom call, or out the door for a flight sets you both up to fail.
- Do I know their schedule? If you think someone is free until lunch and they have an important appointment at 11:45, you’ve misread the moment. If you can find out, find out.
Email works the same way. A friend once gave me good advice: the best time to send an email is the time the person wants to receive it. Friday afternoon may be the best time for me to send something because I want it off my list. That doesn’t make it the best time for you to receive it.
What role are you asking them to play?
Tell the person what their role is in the conversation. If you don’t, they’ll guess, and they may guess wrong. You may need a decision, but they may offer an opinion instead.
I once worked with a woman, a sergeant major in the Army, who had a daughter who was also in the Army. In a particular conversation, her daughter asked her to listen as a mom, not as a sergeant major. Her daughter named the role, and it changed how her mother listened to her.
Most conversations put the other person in one of three roles:
- For your information. This is situational awareness. Know that this is happening, but you don’t need to do anything yet.
- I need feedback. I want your guidance and input. Shoot holes in it.
- I need a decision. I want a yes or a no so we can finalize this.
The role shapes how much time you need. If you want feedback, you might talk for one minute and leave four for them to respond. If you need a decision, say so up front. Someone who feels scattered may not be ready to decide, and they deserve to know that’s what you’re asking. Once it’s a decision, stop discussing it. Make the call and move on. I explain why in Just Saying episode 184, Getting to No Faster.
Why do leaders need room to respond?
If you dominate the conversation, the other person has no room to respond. Busy people need time and space to say something, which means you have to stop talking and allow them to respond
Build that space in. Leave time at the end, and give them permission to react, push back, or ask a question. That turns a one-way briefing into a conversation. When you talk to people who are genuinely busy and burdened, beware. More importantly, be aware.
How can The BRIEF Lab help
At The BRIEF Lab, we help teams communicate with clarity and brevity, so they can get to the point and keep the attention of the people they most need to reach, including leaders with no time to spare. Learn more at thebrieflab.com, and listen to the full episode of Just Saying.
Joseph McCormack first shared these ideas in the Just Saying podcast Ep. 276: 5 Mistakes when communicating to busy, burdened leaders