How To

February 7, 2022

Lessons from a management expert: How to run a great one-to-one

Sathya Smith has been a VC, an adviser and now a founder. She gives her advice on how managers and staff can get the most from their 1-2-1s

Amy Lewin

4 min read

Sathya Smith is an engineer, a tech adviser, former venture partner at Local Globe and, now, a founder. She runs Piper, a startup hoping to help people become better managers. She explained to Startup Life what a one-to-one is for — and what it’s not for.

A one-to-one is not a status update meeting

This is where most managers make a mistake. A one-to-one should be to make sure the individual and their manager are aligned with the company goals, the team goals and personal goals. And it’s an opportunity for managers to give feedback, to coach and mentor the individual to get to a common goal. So, if someone has run into difficulties with a project and says, “I don’t know how to unstick myself”, the one-to-one is to work on the process of unsticking them, rather than saying, “Why is this project late?”

Use your first few one-to-ones with somebody to understand how they work

You want to know: What motivates them? Are they a morning or an afternoon person? Do they prefer to get feedback via Slack or to have you talk them through it? Spend a lot of time getting to know how one another works, and then adapt your style of management to that individual.


Set an agenda for your one-to-ones

This will usually include high-level things like personal career plans and also personal issues — like, “I have a sick child and that’s impacting my work” — and team dynamics. Most questions an individual will have will fall into one of those categories.

Encourage your employee to take ownership of the meeting

Share your agenda doc with them and tell them to think about what they want to talk about. Set expectations: tell them you want to see the agenda filled out in advance. Let them know this time is sacred; a time when a manager is solely focusing on that employee. Use the shared agenda doc to capture notes and actions; this will make sure you’re both aligned, and you don’t leave the meeting with one person thinking you said A and the other thinking you said B.

As a manager, if you say you’re going to get something done, get it done

Prepare for one-to-ones

Look at the agenda in advance, and make sure you have completed any action items from the last meeting. Employees often have to chase up managers for small things, like approvals. As a manager, if you say you’re going to get something done, get it done. On the flip side, if an employee doesn’t have much to say week after week, that’s a red flag; are they not thinking about their career? Are things happening that they’re not comfortable sharing with you? It could mean that they’re not motivated or driven, and looking for a new job.

Always ask these two questions

1/ Are you feeling supported by your team? Especially in remote working environments, it’s harder to see how teams are interacting.

2/ Am I, your manager, supporting you enough? Employees tend to be nervous about giving feedback to their manager, so be open and ask them pointed questions — like “What are some areas I should be improving on? Is there anything I did last week that you have feedback on?” — to make them comfortable enough to share.

Hold regular one-to-ones — and do not miss them

Having a one-to-one every week is ideal. Managers end up becoming a proxy for the company when you’re remote working — they’re the first line of support for an employee — so you want to make sure they’re accessible.

Make sure the employee does most of the talking

It’s a big red flag if the manager talks most of the time. That happens a lot: managers feel like they have wisdom to share!

On the subject of... one-to-ones

🐦 The experts at one-to-ones, according to the people of Twitter. 

👉 One-to-ones are my most valuable meetings; here’s how I run them. An oldie but a good ‘un from Mathilde Collin, founder of Front.

📖 A pretty good guide to running one-to-ones. Pulled together for, we assume, SEO purposes by meeting startup Fellow — but very useful nonetheless.

🤔 The three kinds of one-to-ones: the update, the vent and the disaster. Here’s how to deal with each of them.


🙋 Good questions to ask in a one-to-one. From a16z.

🙌 The unreasonable effectiveness of one-to-ones. They work in your personal life too.

Amy Lewin

Amy Lewin is Sifted’s editor and cohost of Startup Europe — The Sifted Podcast , and writes Up Round, a weekly newsletter on VC. Follow her on X and LinkedIn