How to not suck at 1:1 meetings
A product leader's manual to not be that leader whose 1:1s do more harm than good.
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I once had a leader whose 1:1 meetings were so bad that I celebrated when he would cancel them. He loved the sound of his voice. He was always proactively offering ādeepā life lessons, often related to anecdotes of one of his volunteering trips to developing countries. I later discovered that the anecdotes were not even tailored to me ā all PMs would get the same āinspiringā stories in their 1:1s. I always thought ādamn, I could be doing some real work, instead I am listening to a story about a street musician called Manoloā. I would leave the meeting more confused than when I came in and just went back to do my work.
I eventually quit that job, letting go of a bunch of unvested shares, largely because of this leader (not only his 1:1s). While that is an extreme case, I have had my fair share of bad 1:1s. Iāve also been blessed with many outstanding leaders who really knew how to run those meetings. As a cherry on top, I've worked with talent development in my career before product. Because of all this, I feel I can teach a thing or two to take your 1:1s to the next level.
As a leader, what is the benefit of 1:1 meetings?
One of product leaders' most important jobs is supporting the growth of their PM reports. This is not out of the goodness of their hearts. PMs that are growing and improving will deliver more business results.
Also, according to Daniel Pink, there are three drivers of intrinsic motivation: autonomy, mastery, and purpose. Motivated people are more likely to go the extra mile, again delivering better business results. And guess what? The one-on-one meeting is a great vehicle for working on all three:
Mastery. The product leader supports the development of their reports by helping the Product Manager grow through a balance of teaching (mentoring), asking the right questions (coaching), and giving clear feedback.
Autonomy. The product leader can use coaching (asking questions) to help their direct reports reach their own conclusions and answers. Also, PMs gain more autonomy as they develop mastery in their craft.
Purpose. Last but not least, 1:1s are a great medium for conveying the importance of what the PM is working on in relation to the company's and product's priorities.
But how do you deliver a good one-on-one meeting as a leader?
The direct report owns the agenda
One-on-one meetings are for the benefit of the direct report. They own the agenda, not their leader.
I always make this clear to my direct reports: the 1:1 will be as useful to them as the quality of the topics they bring to it. I nudge them to prepare the topics in advance. They should not treat as a random conversation with their leader, but a leverage for them and their work.
Prepare for the meeting
Just because the product manager is bringing in topics to discuss doesn't mean the product leader shouldn't do the same. The difference is that the priority is to go through the report's topics first, going to the leader's topics only if there is enough time. What if there isn't? Then, the leader schedules an ad-roc meeting to address those points, or they wait for the next 1:1.
I prepare for next week's 1:1 on my weekly Watchtower Reflection exercise by thinking about my goals for the next week and how I can achieve them, which often involves talking to my PMs.
One anti-pattern to watch is when the direct report asks to prioritize the leader's topics first. Don't let this happen. They are either trying to please you (at their own expense), or they didn't prepare enough for the meeting, which is a bad sign.
Frequency and length
Different people have different needs.
That said, I gravitate between weekly for most PMs and fortnightly for more senior ones who want less hand-holding (and are able to).
I also strongly prefer 1 hour or at least 45 minutes in length. I think 30 minutes or less is too rushed, without any space for personal chit-chat to connect with the person. If all the topics are done before the end of the meeting, you can always end early or double down on the chit-chat.
Treat 1:1s as a priority
Some leaders often cancel 1:1s, which signals that developing their people is not their biggest priority. Big no-no.
Unless all hell breaks loose, I go to great lengths not to cancel 1:1s ā once, I drove for 30 minutes to find a cellphone signal after a typhoon had destroyed the city's electrical and communications grid:
But if you really have to cancel it, you should propose a new timing on the cancellation itself. Make sure not to miss this one.
Don't talk more than your follower
Don't be the leader who loves the sound of their voice. If you are speaking too much, you are not giving your product managers space to ask questions and address their biggest issues. You might also be overindexing on teaching (mentoring) instead of supporting the PM to find their own answer (coaching).
Create rapport, especially in new relationships
While AI might replace us all, we still must connect as human beings to work better together. No product manager will be transparent about issues if they don't trust you as a person. Connect to their lives, ask and share about the weekend, vacation plans, random pet peeves, etc.
1:1s are not status report meetings - don't neglect the PM's career and life
Another anti-pattern is talking only about current work, not future aspirations and expectations. You have to discuss what the person wants for their career: What is their ideal next role? Do they dream of doing something? Are they being able to get the most out of life?
If, like me, you are not an outstanding conversationist, you can use something like the Magic Questions framework:
Ask one or more of these questions and ask your direct report to score it from 1 to 5.
Is what you are doing now at work leading you toward your career vision, 1-5?
How are you feeling about your life at work, 1-5?
How are you feeling about your personal life, 1-5?
How are you feeling about your physical work setup, whether at home or the office, 1-5?
How are we performing as a company, 1-5?
What is it like to work with the rest of the team (your peers), 1-5?
What is it like to work with me, 1-5?
The scale is:
1 - It couldnāt be any worse
3 - Meeting expectations
5 - It couldnāt be any better
Then ask āwhat would get it to the next scoring level?ā to discuss improvement plans.
Document decisions and follow-up
In your 1:1s, you should agree on to-dos and decisions, which should be documentedāideally by the direct report.
Follow up in the next 1:1s and in between meetings whenever appropriate. If your report finds out that you forgot those tasks, they will be less likely to execute them.
Obviously, if you are assigned a to-do, don't let the PM down by not doing it. Walk the talk.
I tend to favor simplicity when tracking this. For example, I share a 1:1 Notion page with my direct report, including meeting notes by date and a category for open to-dos.