1:1s with Direct Reports

Tech Manager Handbook: A Series

What’s the point?

1:1s (“one-on-ones”) are an important way to stay in touch with your employees and they are your employee’s primary access point to you. They serve many purposes:

• Providing tactical advice on their project work
• Giving and seeking feedback
• Managing their career paths and goals
• Discussing issues that may be affecting their ability to work or succeed (personal or professional)
• Debating product and/or business strategy and vision; especially sharing broader context that may impact their work
• Building general rapport and trust with the employee
• Literally anything else that is on their mind

Who drives?

The 1:1 agenda should be owned by the employee. You should remind your employees of this fact every so often, especially if 1:1s with a particular employee are routinely unproductive. If they don’t come prepared with specific things to talk about, employees will often default to getting in the weeds and providing a series of tactical updates about specific projects (often not a good use of either of your time). You should set an expectation that 1:1s can end early and give/take the time back if there isn’t anything meaningful to discuss (in a respectful way). You will find that your strongest performers will generally have the most to talk about and will also likely be the most productive 1:1 conversations.

You can ask them to send you a rough outline a few hours or a day in advance of the 1:1 to force a little more structure (there are fancy tools for this kind of thing but honestly a simple shared Google Doc will do the job). This will force the employee to put some thought into what they want to discuss and also serve as a place to track action items, career goals, document light-weight feedback, etc. — this can be a particularly useful practice when trying to create accountability for low performers.

You can always add things to the agenda yourself (they may “own” the agenda but you can add to it). The types of things you might add to the agenda are check-ins on their career goals, specific feedback you have for them, additional context that will help with their project work, etc.

How frequently should you meet?

This can depend on a number of factors ranging from if the employee is an individual contributor (“IC”) or manager, their relative seniority, how well they are performing, how long you’ve worked together, etc. The default setting for ICs should be a weekly 30 minute 1:1 (not rocket science). However, what people often forget is that for more senior employees or those that you’ve established a high degree of trust and confidence, you should consider reducing cadence and giving time back (e.g. switch to bi-weekly, monthly, whatever feels right). This can be a massive help if you happen to lead a large team, have a very busy schedule, or routinely find yourself burning out from too many 1:1s. It is better to have less-frequent high-quality check-ins than more-frequent low-quality ones.

Be deliberate about how you organize your 1:1s

Pay attention to how 1:1s affect you: do you find back-to-back-to-back-to-back 30 minute conversations draining? Do you find 1:1s with particular individuals uninteresting or draining? Adapt how you schedule your 1:1s to best suit your schedule and needs. Do you prefer to set aside a single day to hammer them out all in a row? Do you prefer to space them throughout the week? Do you prefer having 1:1s in the morning or in the afternoon? You can always ask employees to move lower-priority scheduling conflicts (but be mindful of their important recurring meetings, typical working hours, and/or local time-zones when scheduling). Don’t forget to book rooms for 1:1s with remote employees (if you or they happen to be in the office).

Mix it up

One way to break the cycle and prevent 1:1s from becoming repetitive and boring is to mix-up how and where you do them. Live nearby or work in the same office? Consider grabbing a coffee or holding a 1:1 over lunch. Nice weather outside? Consider making it a walking 1:1. At the end of the week? Consider grabbing a beer before heading home for the day. Different circumstances can lead to different kinds of conversations and often more meaningful ones. It sounds silly, but even subtle differences in how you open a 1:1 can lead to different kinds of conversations from “what’s up?” to “what’s new?” to “what’s on your mind?”

Navigating difficult discussion topics

Always aim to be objective, constructive, and direct when having difficult conversations (sounds obvious, I know). If you initiate what might be a difficult discussion (e.g. giving feedback) you will (hopefully) have thought about exactly what it is you want to communicate and have prepared some brief remarks as well as concrete/specific examples ahead of time.

If an employee makes an unusual or unexpected request (e.g. excessive amount of vacation) remember that you don’t need to give them a definitive answer on the spot. It is more than okay to simply share some initial thoughts but admit that you will need some time to think about it but be sure to give them a date that you will follow-up with them by. Then use the time you have to talk it through with your lead, seek advice from your peers, or ping HR depending on the nature of the situation. If you aren’t sure if you should or shouldn’t loop-in your lead or HR, then you probably should.

Employees can sometimes get emotional, especially during or following a difficult conversation. If this happens you should offer to break and pick-up the discussion again later. If after a 1:1 you can tell that the employee is still a bit rattled you can also suggest to them that they take a few hours or even take off the rest of the day. If you know you are going to have a difficult conversation with someone, it is usually best to schedule it later in the day. Consider if you need privacy and should book a room (if in the office), but also consider what kind of signal booking a room might send to someone if you typically meet in an open common area.

Lastly, always try to avoid catching them completely off-guard. Nobody likes being surprised by critical or negative feedback so be sure to give them a heads-up over Slack and try to frame things in a positive light. After a brief sentence or two touching on the issue, let them know that it might be a good idea to chat more about it in your next 1:1. This enables you to provide a bit of real-time feedback and prevents any surprises.

Final thoughts

1:1s are an important staple in how you stay connected with each individual on your team, provide coaching, build trust, and get to know one another as people. Realize that you can always change cadence, style, or structure to ensure they remain a good use of both your and their time. Above all else, always show up and be ready to listen.