Resource Download

Enter your email address and we'll send you a link to download this resource:
60 questions for your one-on-ones
Thank you! We've just sent you an email with this resource. Check your inbox now!
Oops! Something went wrong while submitting the form.
10 Common Challenges With Employee One-on-Ones

10 Common Challenges With Employee One-on-Ones

Free Resource

One-on-one (1:1) meetings between a manager and direct report are a growing trend in companies today, highly prevalent in the tech and start-up community. They are an excellent opportunity for managers to have an open-ended conversation with the members of their team. Turning the 1:1 into an effective growth accelerator comes with its challenges. Let’s explore 10 of the most common challenges we hear from managers attempting to 1:1 with their teams.

1. They take time

Managers already have more meetings than the average employee. Trying to find regular recurring meeting slots to hold with each direct report can feel overwhelming. They also require energy, which means doing them on a Friday afternoon is probably not the right time for a productive discussion.

What we find works best: Choose one afternoon every other week on Wednesday or Thursday and block out your schedule. Use this time for bi-weekly 1:1 discussions with your team.

2. They require quiet space

More and more offices today have an open-layout. This typically means there is limited conference room space, and leaves you with no option but to hold your 1:1 in the common space, where privacy is lacking.

What we find works best: Use your judgement here — some employees are completely comfortable having this discussion in the open, and may prefer it. Others want closed doors. If you need to get creative, take a walk over to a local coffee shop and hold it there.

3. They are hard to structure

Given their casual nature, there is no standard for structuring the conversation or how it should evolve over time. All sorts of factors contribute to the flow of discussion including seniority level, personality, and dynamic between manager & direct report.

What we find works best: Try using the continue, start, stop methodology. Make a list of what your direct report would like to continue working on, what they would like to start working on (addressing and learnings from previous trial & errors), and what they should stop doing. Pick one thing to focus on between now and the next 1:1. Be mindful and don’t do all the talking — let your direct report speak at least 50% of the time, if not more, with you simply guiding the discussion.

4. They don’t feel effective

A 1:1 is only as effective as the conversation itself. Often times, these discussions digress into questions about the company, etc. Although answering these questions are okay, 1:1’s should remain focused on the employee, their current role and projects. They are not a replacement for the daily business conversations that should be happening at the team level.

What we find works best: If the conversation starts to go off on a tangent, interrupt, write it down as an offline follow-up and refocus. Commit to this and remain aware of where the conversation is headed.

5. Their content gets lost

1:1 discussions often lack a well documented trail. Which means, it takes a super-manager to remember each discussion, each week, with each employee.

What we find works best: Reserve 5 minutes at the end of each session to jot down the key takeaways on your mobile device while you are holding your employee 1-on-1. Email them out immediately to you and your direct report so there is a paper trail. Each subsequent meeting, start by reviewing the take-aways from your last meeting, addressing any follow-ups you may have missed.

6. They sometimes feel forced & awkward

We often hear from both managers and employees that the 1:1 conversations feel awkward. There are myriad reasons for why you may find it hard to connect with your direct report — you have a super-star on your hands who doesn’t need much coaching; your direct report is extremely shy or an introvert; various communication roadblocks hinder mutual understanding; and all sorts of external factors like personal life, mental health, engagement, etc.

What we find works best: If discussion isn’t flowing naturally between you and your direct report, keep it concise and focused. Try asking your direct report to write down their “continue, start, stop” items before the meeting, giving them time to think it through. They can even email you the list ahead of time, so you both come more prepared, and there are fewer surprises / awkward pauses.

7. They are regularly skipped

Quick, 30 minute 1:1 chats are the easiest to push off and reschedule, especially at startups… that is, until you realize that months have gone by and you haven’t sat down individually with your direct report. This can lead to a lack of confidence and trust between manager & direct report, or sheer frustration.

What we find works best: As tempting as it is to reschedule and reprioritize — don’t. Try your best to keep these at consistent intervals, and if you have to reschedule, make sure to do so in the same week. Prioritize your team!

8. They can turn into a gossip-session

If your direct report feels comfortable around you, it can be easy to turn the conversation into a venting exchange about your frustrations with the company, or other team members.

What we find works best: Venting is helpful, but try to refrain from being the person doing the venting and instead guide the conversation to remain constructive. As the manager, you must remain neutral, calm and positive about the team & company.

9. They are uncomfortable to end

If you’re experiencing one or more of the above mentioned challenges (in particular 3, 4, 5, 6 or 8), you are probably experiencing this one too. Figuring out the right note to end a 1:1 on can be tricky. The conversation may have gone off track, gotten tense or you might need to end abruptly to make your next meeting.

What we find works best: Keep a clear sense of time during the meeting. Give yourselves a 10 minute warning, and as suggested above, reserve the last 5 minutes at the end of each session to document any next steps. Plan for a follow-up meeting if any pressing issues remain unaddressed. And most importantly, end on a positive note.

10. Your direct report has more experience than you

Are you unsure about how to guide your direct report? This happens all the time. As companies grow, managers promoted from within are often less experienced than some of the new hires they recruit for their team — and this is great! Hiring team members who are better than you raises the bar for the entire team.

What we find works best: Think through some thought-provoking questions that will get your direct report to open up to you, and maybe teach you something you don’t know. If they need advice on something you feel unequipped to handle, support them by helping to think through different approaches and resources without prescribing the solution. Managers don’t have to be the most experienced on the team, but they do have to be great at listening, organizing and motivating.