Last week, a senior executive in my company did a session on Having Effective One-To-Ones. It sounds like a really simple topic, but I walked away from it feeling like I learnt a bunch of new things. Here are my key takeaways:
Shitty One-To-Ones
Tell me if any of these scenarios sound familiar to you:
The Ramble: You have a lot on your mind. Your manager asks, “So how’s work going?” and you launch into a tirade of different problems, wins, and your frustrations that John from Legal is being such a pain in the ass. Your manager’s questions only serve to bring the conversation down another rabbit hole. You walk away from the one-to-one feeling even more confused than ever.
The Status Update: You spend an hour preparing updates about your work, and go through it in painstaking detail with your manager. Your manager’s eyes start glazing over. She fiddles with her phone. When your 30 minutes are up, your manager says, “Okay great work!” and leaves you wondering whether the past 1.5 hours were a good use of your time.
The Rush Through: You spend 25 minutes chatting with your manager about how your weekends were, then rush through the last 5 minutes stumbling through a few issues that you need help on. Because your manager has another meeting, she gives you one-line pieces of advice instead of the thoughtful guidance you were hoping for.
I’ve delivered and been on the receiving end of these sucky one-to-ones over the past 12 years. Whenever this happens, it can be frustrating, annoying and cause me to question what I’m doing with my life.
But the truth is, one-to-ones don’t have to be sucky. If you do them right, they have the potential to unlock opportunities, make your work easier, and accelerate your career.
What Can Great One-To-Ones Do For You?
They can accelerate your career: Your manager has the biggest influence on your immediate career prospects. This is a hard fact of work life, no matter how much you love or hate your manager. And your job is to make it as easy as possible for your manager to know your work, so that she can make the best case for you when it comes to promotion decisions. However, most managers aren’t micromanaging every email or meeting you’re doing, so they rely on one-to-ones to understand your work and how you’re coping. If you do your one-to-ones well, your manager will have a MUCH easier time fighting for a promotion for you, rather than scratch her head trying to justify why you deserve one.
They can make your life easier: Your manager’s job is to unlock shitty situations or challenges, so that you can focus on doing your best work. Maybe another team isn’t giving you the data you need. Or maybe you’re stuck because you have no idea how to approach this presentation. Your manager WANTS to help you unblock these, but she’s also incredibly busy. Your one-to-one is often the only opportunity in a week you’ll get to get her advice and help. But you need to manage it well so that you can actually zoom into the key issues you need.
They can improve your decision-making: One-to-ones are an opportunity to step back from the daily grind and recalibrate how you’re working. Asking for your manager’s advice is also a great way to check your assumptions and see if you’re on the right track.
Despite these benefits, we probably prepare less for a one-to-one with our manager than we might do with say, a C-level person or a client. Why is that? More often than not, it’s because we feel psychologically safe to share whatever we want with our manager. That’s really good, but it also lulls us towards a laissez-faire approach toward our one-to-ones, which completely jeopardises the above benefits.
To understand why, it’s important to first understand your manager’s mindset.
A Quick Note On Your Manager’s Mindset
Your manager’s time is valuable. Your manager is probably feeling stressed. As busy as you think you are, your manager is probably experiencing 3X the stress that you’re currently feeling. Not only does she have to tackle her own work, she also has to deal with People Management issues which, in my experience, are way tougher than the day-to-day work. She has to answer to her bosses, shield her team away from distractions, showcase and fight for her team, and be aware of what each and every member is doing & feeling. Above all of that, she’s spending a dedicated 30 minutes a week with you, for your sake. With that in mind, is it still a good idea to spend that 30 minutes just randomly talking about stuff that doesn’t matter?
Your manager doesn’t (really) want to know the details. This might not apply to everyone, since some managers like to micro-manage. But from my experience, especially at the more senior levels, it’s cognitively impossible for most managers to dive into the details for every team member. So while your manager WANTS to know that things are on track, she doesn’t necessarily want the excruciating details about your discussion with Joey from Marketing. She’s got more pressing issues on her mind, and so you’d be doing her a huge favour by filtering out the noise and honing down to just the most important topics.
Your manager wants to help. Your manager wants you to succeed. When you deliver great work, it looks good on her as well. She’s highly incentivised to help you reach your goals, and she has access to other bosses who could help or hinder you. However, she needs to walk a fine balance between supporting you and micromanaging your work. She’ll only step in when you need her help, so it’s your job to identify the key areas where you need that additional support from her.
With this in mind, let’s explore a couple of ways to have great one-to-ones that don’t suck.
Tip 1: Be Clear About What You Want
One-to-ones are YOUR responsibility, not your manager’s. You should be the one setting the agenda and leading the conversation. Nothing is more annoying to a manager than working with a passive teammate who isn’t taking ownership and driving things forward.
Remember: One-to-ones are sometimes the only window you’ll get to highlight your work and ask for support. So it’s critical that you spend your 30 minutes well by preparing for it in advance. Focus on the highest-leverage items for you to succeed, and write it out beforehand. Send it to your manager (see the next point on sending a pre-read). If you’re winging the agenda while you’re walking into the room, you’ve already failed.
Your agenda doesn’t have to follow the same format every week. Some weeks, you might go through a laundry list where you need quick approvals for, and other times you might spend your whole 30 minutes discussing a thorny problem. But whatever the format, be clear about what you’d like to talk about beforehand, so that you make good use of your time.
Tip 2: Send a Pre-Read
This, in my opinion, is the best way to give status updates. Here are a couple of benefits of writing out your updates instead of delivering them verbally:
- It doesn’t take up time on stuff that you don’t need your manager’s input on (remember: your manager’s time is valuable).
- Writing also forces you to distill your projects into the essential points instead of rambling. This not only helps your manager zoom into the key issues, but it also trains you to be succinct when you need to talk to senior management.
- Consolidating all your updates into a rolling doc also makes it super easy to go back and review your work. This comes in handy when you’re preparing your performance reviews, since you already have all your wins/updates all in one place
I have a rolling Google doc which is shared with my manager. I used to structure it according to my OKRs, but I’m now trying out a new format where I only focus on only the most important updates for the week. Here’s a sample of my updates (with details removed) for last week:
- Revenue
- Project A: Person A has kicked off <Project> discussions with specialist and partnerships team. Timeline (here), R&Rs (here). Further discussion needed to hone down R&Rs
- Project B: Set up 121s with product team to discuss 3 opportunity areas for us to own: 1) Opportunity A, 2) Opportunity B, 3) Opportunity C
- Customer Projects
- Case Study: We saw a jump in <metric A>, but <metric B> saw some declines. Meeting with specialist next week to dig into these numbers further.
- Client project: Kicked off discussion on <Project>. Purpose is to prove the impact of <initiative>. Will need close support as this is the first time they are running this.
- People
- Conducted milestone assessments for Person A and Person B on <topic>. Both did well, shared some guidance on sales strategies based on personal experience.
As you can tell, these are quick, high-level updates on key projects I’m running but don’t need my manager’s help on, for now. I keep each update to 2-3 sentences max and link out to any key documents if she needs any additional context.
My manager reads these before our one-to-one, so she knows what I’m up to. Unless she has questions, we won’t need to spend time discussing them unless she has a question or advice, which saves time while still giving me an opportunity to highlight my work.
Tip 3: Have A Section For Discussion Points
I’ll then have a separate section titled “Discussion Points”, where I’ll ask for her thoughts around several items that I need help in, or to simply bounce ideas off. This is where we’ll spend the bulk of our time during our one-to-one, since it’s here I need help in. Here’s what my discussion points from last week look like:
- Revenue
- Client Partnership: I wanted to align on our positioning and next steps for <partnership>. My thoughts are: 1) Positioning A, 2) Positioning B, 3) Next Steps. I would like to spend some time discussing these and check if we are aligned
- Client Pitch: Here is the deck for our upcoming pitch. Purpose is to show a concrete plan to drive ROI for <client> Would love to spend some time discussing this and see if it can be improved further
- Community:
- Event: Have we heard back from <Person A> yet? In terms of engaging <Person B>, do we have a topic in mind for them to speak on, or should I propose one?
- Project: Summary of <Project A> progress (here). Would you like to surface these to <Person B> to highlight the work we’ve done in this area?
Here, I’m primarily using my discussion to seek alignment and advice. I’m also using it as an opportunity to nudge a few pending action items from her.
Tip 4: Write Out Your Decisions & Key Actions
Once you have these points written out, 80% of your work is done. When you walk into your one-to-one, you’ll know exactly what you need to talk about and what points you need your manager’s input on. You can be sure that you’ll be spending your time just on the highest-impact items, instead of wasting time talking about your weekend.
The last thing to do is to write your decisions and key actions while you’re discussing them. For example, for the discussion points above I might write:
- Client Partnership: Aligned on positioning, wait till we hear back from client on the progress report that we sent before regrouping on the next steps
- Event: <Person A> has agreed to speak, need to change the speaking slot to 1.30pm. Sync up with <Person B> on speaking topic
- Project: Work surfaced to <Person B> and also to <Person C>
Why do I like writing out the decisions and actions? Because people often interpret the same information differently, even in the same meeting! I’ve had countless occasions where I massively misinterpreted what my manager wanted, leading to lots of wasted time. Writing out the decisions on paper as they happen minimizes the likelihood of misalignment.
When your one-to-one is over, simply copy and paste everything you’ve written into an “Appendix” section of past One-to-One notes. That way, you’ll have a written record of everything you’ve discussed with your manager. This has two benefits:
- You can review these to improve the quality of your decision-making. E.g. Say a project that you were working on failed, you can go back and review what your assumptions and decisions were back then, and learn from your mistakes
- You can easily compile evidence for your performance review, since all your work is in one place
- Your manager can revisit these when she needs to fight for your ratings and promotion during calibrations
Adapt What Works For You
Of course, every person has a different style. Some may hate writing updates, and others may think two or three sentences is insufficient. These are simply tips and a process that I’ve found useful (and interesting!). Take what’s useful, and discard the rest.
No matter what your format, it’s important to remember the principles behind it:
- Be prepared for your one-to-ones
- Spend time on discussions, not low-value updates
- Write stuff down – it’s useful!
I’m curious to hear how you run your one-to-ones. And for managers out there, to hear if you’ve had any particularly great (or horror) stories of memorable one-to-ones. Let me know in the comments!
