If you’re a leader of a team, I hope there are some pointers in here for you.
1-1 conversations are a staple of the boss-employee relationship. But so many of us just check the box when we could be having much richer, more productive conversations. Here are some tips on how to do them well.
Modern Mentor is hosted by Rachel Cooke. A transcript is available at Simplecast.
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Hey, it’s Rachel Cooke, your Modern Mentor. I’m the founder of Lead Above Noise—a firm specializing in helping teams and organizations create better working experiences in service of better results.
I recently had the chance to reconnect with one of my very first – and favorite – managers. It’s been a long time since I worked for him. But my memories of his leadership have aged well. And I got to tell him so.
He took it with grace. But also wanted to know, specifically, what I remembered most. And I said, “You know – I think it was our one-on-ones. You did them better than any leader I had before or after you. And they really fueled the path that led me to where I am today.”
Or something like that. But really, we had the absolute best – most engaging, most productive, most supportive one-on-one conversations. And I’ve been thinking about what magic they held. It was a lot.
But today I’d love to share some of the elements I recall most fondly.
If you’re a leader of a team, I hope there are some pointers in here for you. And if you’re an employee and you’re feeling hungry for a little more development from your leader, maybe gently forward this episode their way. Or pull out an insight or two, letting them know you’d like to try something a little different in your next 1-1 conversation.
Through the course of your career, you’re likely to have many conversations that meet the numeric criteria of a 1-1. But a real 1-1 conversation, in my book, is defined by purpose more than math.
A true 1-1 conversation for me is all about the employee and their development. It’s not a time for project updates, for talk of deadlines or procedure or customer needs.
It’s a time for you, the employee, to talk about whatever feels important for you in the moment to help you grow, develop, and feel a sense of momentum in your career.
This is something my boss understood intuitively. Any time I’d start to veer into an update of any sort he’d push back and remind me we’d have plenty of time for those conversations later. These 1-1s were meant to be about me and what I needed from him, be it coaching, advice, support, feedback – you know, all the stuff that makes you just better.
As in, he was totally present in these conversations. He’d never cancel unless something truly urgent popped up, and he was always fully present with me. His laptop was closed (this was pre-Zoom meetings, of course), and his phone, put away.
I never felt like he was itching to leave. He would listen fully. He’d ask me questions about my goals, my sense of progress, and what I needed from him. These meetings were neither long nor frequent – maybe 30 minutes once a month? But they always felt so full of substance for me.
So my boss played an important role in these meetings. He did the heavy lifting of showing up and being present.
But my responsibility for how effective these meetings were was even greater.
I was in charge of planning what we would discuss. And this forced me to be thoughtful and really take responsibility for my own career.
I’d map out the agenda about a week ahead of our meeting. This challenged me to think about what I wanted to cover, and also gave him an opportunity to do any relevant prep.
So if, for example, I wanted to use our time together to get feedback on my recent performance, he’d have a chance to do some reflecting – and maybe reach out to some of his colleagues, as well – to put together some thoughtful notes for me.
If what I wanted was to find ways to ready myself for a promotion, he might use that advance notice to find out if any jobs were going to open soon. Or he might ask a colleague of his to serve as a mentor for me.
And if what I wanted was his help in expanding my internal network, he’d use that time to put together a list of people he’d like to connect me with.
By giving me ownership of the agenda, he really did challenge me to ask myself – what are my goals right now? What will most help me to move forward right now? And what specifically – be it support, feedback, introductions – do I need from my boss?
He always had a pen in hand during these 1-1 meetings. And he made sure that whatever we’d discussed had a series of actions or next steps attached.
A great 1-1 conversation doesn’t just stand on its own. It isn’t just a bit of dialog or a touch base. It should be a means of defining next steps – actions, ownership, and timelines – all designed to further the employee’s growth and development.
Following our 1-1s he’d shoot me a quick email with a bulleted list of the actions he’d captured. Which held us both accountable to doing the things we’d agreed to.
Action and accountability are key.
I grew up watching sitcoms, which I loved for their bite-sized simplicity. You could watch them in any order because each episode was a complete story. Beginning, middle, and end.
Today, I can’t tolerate a sitcom anymore. With or without the laugh track, they feel kind of basic for me. Give me a great show where the story unfolds over the course of all the episodes. One big, juicy story that gets told over time.
Through this lens, my boss was more Netflix than Network in how he drove our 1-1s. Like, he really threaded that needle so each episode – I mean, 1-1 – felt not like a standalone story, but rather a chapter in something more epic. Like, my career.
Each time we came together he’d start by asking a question or two relevant to our last conversation. And he’d ensure that whatever we’d be covering this time around felt like a build-upon rather than a sharp left or right.
When we’d come together for a 1-1, I might be asking him for advice on how to pursue a promotion into a role that just opened. And before he’d offer any up he might say something like, “Last time we met you’d asked me to introduce you to some senior leaders in the Executive Development team. Did you manage to connect with them, and what advice did they offer you that might support your goal of getting this promotion?”
OK – I’m not saying the storyline is quite as propulsive as the dramas I stream. But I am saying there’s something really valuable in the feeling of continuity - of knowing that what happened last time will inform what happens this time, and that if I keep on pulling that thread through these conversations, I have an excellent chance of landing a killer season finale.
So thank you, former boss (you know who you are) for the gift of your time, your attention, your support, and your partnership in helping me grow to where I’m proud to be today.
And I hope you, listener, have found a piece of wisdom in here that you might just pick up and use in crafting your next 1-1 with a boss or team member.
Join me next week for another great episode. Until then, visit my website at leadabovenoise.com if your organization is looking to dial up its Employee Experience or deliver some leadership development that activates change. You can follow Modern Mentor on Apple Podcasts, Spotify, or wherever you listen to podcasts. Find and follow me on LinkedIn. Thanks so much for listening and have a successful week.