When’s the last time you really sat down and had a one-on-one with your team members? Answer honestly, because I know that I probably should be having more of these myself. Meeting individually with your team members is incredibly powerful, motivating and impactful—but most business owners just aren’t doing it.
Some of these HR topics might seem dry and boring to people, but they are critically important if you’re trying to grow a business, whether it’s a remote business or a standard office setup.
I’ve been in both situations, and I’ll say that remote work cultures are even harder to manage because there’s less incidental face-to-face time. It’s really easy for people to become disengaged in remote environments and some people just aren’t a fit for working remotely. People who feel like they’re stuck in a cave by themselves are going to end up quitting because they’re social creatures.
That being said, developers and designers tend to work really well remotely. Generally speaking, creatives who tend to do their best work alone are fine working remotely (for the most part). But for other aspects of marketing and strategy where you need to collaborate with people, talk about ideas, and meet more in person, face-to-face time is crucial.
Learn More: The Definitive Guide to Building a Remote Team
Let’s say I block out time on Mondays for one-on-ones. Everybody gets 30 minutes or so. If we need to talk about something else we can just set up another meeting. I actually used to hate meetings, but as a business owner I couldn’t help but slowly realize the importance of one-on-ones. In a way, they’re every business owner’s responsibility.
Okay, now I have time blocked out—but what am I talking about with my team member? First and foremost: make sure these meetings are always about the employee, not about you. Too many companies turn one-on-ones into performance reviews or other anxiety-inducing experiences where an employee feels on edge. That’s not how you should do these things.
Typically, what I like to do is start things off with regular conversation about personal life and goals. The person I’m chatting with can segue into talking about work, and often they’ll even give an update without you asking. They’ll also talk about a problem that they’re facing, something that’s frustrating them or bothering them. From there, you can decide how you want to take the conversation. But the point is you have to start by listening.
This isn’t necessarily easy to do. As the business owner and team leader, your natural inclination is most likely to make the meeting about yourself. You probably have a dozen other things competing for your attention that day. But you have to resist the temptation to check your phone constantly and realize that the meeting is for the employee.
The problem with turning the meeting into a performance review that’s only about the company or only about someone’s job description is that it’s no longer a conversation—it’s just a report. And you don’t need to do that in a face-to-face, one-on-one meeting. You’re sort of missing the point entirely and wasting everyone’s time.
And whenever that happens, people are disengaged during these meetings. They’ll come with answers to what they expect you to ask, but nothing else. Then it’s your job to refocus the conversation on them and make sure they have an agenda when they come back next time. The point of the meeting is for them to have a sounding board.
“I’m sensing that you might be a little disengaged or I’m sensing that there might be something wrong based on A, B and C. I’ve seen this, this and this and that leads me to think this.” Then stop talking. Let them elaborate on what they’re feeling or going through. Let them explain what’s going on. Then say, “Hey, honestly these meetings are for you at the end of the day and they’re to serve you. If you don’t come with some kind of agenda or something on your mind then I’m just going to go into my agenda and then it becomes my meeting.”
These meetings are stepping stones for making sure, in the following order, that:
A) employees are happy with where they’re at
B) they’re performing well
C) they feel comfortable voicing their opinion or discussing new and exciting ideas they have
If I don’t get a good sense of where they’re at on a weekly basis, then I’ll do it every single day until I feel like they’re comfortable with things. This is especially important for new employees who are in the onboarding process. I’ll ask them, “Hey, how are things going? How can I help you?”
Ultimately, even if you’re the owner of the company or some type of director or manager, it’s your job to serve the people who report to you. You want to be a servant-leader. But it’s also your job to hold them accountable. The trick is learning how to do that in the right way.
If you’re the business owner and your business has 100 employees, then obviously you may not have time to meet with every single one of them. At that point, you should only be having one-on-ones with your direct reports. But your managers should be having one-on-ones with all their direct reports, too.
Learn More: How to Onboard New Hires
I really enjoyed having these one-on-ones when I was at Treehouse and other startups before that. Every week I’d get to talk to the CEO and I’d just say things like, “Hey, here’s what’s going on? By the way, I need support here.”
As an aside, at the time, even though our marketing team had eight people, we didn’t have a developer who was dedicated to marketing. My recommendation is that you should always have at least one developer and one designer on the marketing team so you can get things done faster.
There were so many things we wanted to do that required a developer to jump on experiments or new initiatives so we could hit our numbers. And I emphasized this over and over every single week at my meeting. I’d alway say, “Hey, I know we didn’t hit numbers and I know we need to hit numbers. But if I can’t get a developer on my team we’re going to set ourselves up for failure.”
I basically told the CEO that we were going to lose the company if we didn’t get some help on the marketing side. The problem with Treehouse back then was that we had a great product, but none of the developers wanted to work on marketing, which was the only way to scale our way out of near bankruptcy. So I had to make it very clear from day one.
I also had lots of one-on-one meetings with the VP of engineering. I just kept voicing my frustrations over and over and over until they got it. When they finally got it and agreed—that’s when we got things done. I’m fairly certain that if we didn’t have these one-on-ones in the first place, the company would have gone under.
My experience at Treehouse and later at Single Grain taught me that one-on-ones are really important, especially in the nascent stages of a company when you’re trying to grow. We had 54 employees at the time I joined Treehouse, and we were getting bigger and bigger. Today they have almost 200 employees, but they’re still doing those one-on-one meetings.
I would strongly suggest going to Google and searching for how to do a one-on-one. There are some great posts on this topic by Sam Altman. You’ll see that the companies that don’t do one-on-ones typically have disengaged team members who don’t really know what’s going on.
But if you keep people updated and get a sense of where they’re at and how they’re doing, that’s going to help you figure out what the next move is for the company as a whole. Listen to your people, respect what they have to say, keep them accountable, and do your best to support them. Be the leader they deserve.
This post was adapted from Eric’s Facebook Live videos: Growth 90 – DAILY live broadcasts with Eric Siu on marketing and entrepreneurship. Watch the video version of this post:
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