How to Ruin a One on One Meeting

A number of years ago, my boss told me he wanted to have a one on one meeting. He was leaving the organization shortly, and he had never done a one on one meeting with me except on my request, so I knew something was going down.

We sat in his office guest chairs, across from one another, as was his habit. He said he wanted to touch base before he left the organization, and then the meeting began. It turned out to be largely a recitation of my flaws and missteps as an employee over the years we worked together. He was, despite all this, a genial and likable person, so it wasn’t as rough as it could have been. But it still goes down in the annals of terrible meetings in my career.

There was no action to be taken, no follow up, no opportunity for growth. Just an Airing of the Grievances. My own personal Festivus. Thank god there were no feats of strength.

That meeting was years ago, but I still think of it from time to time, especially when the topic of one on one meetings comes up. One on one meetings are one of the great and effective management tools available to law firm owners. There’s a lot of good info out there about how to make the most of your one on one meetings, though I remain partial to the Manager Tools version of how to make these work.

Today, however, I want to spend a moment not on the ways to make a one on one meeting a success, but on the many trapdoors and pitfalls that can ruin a one on one in meeting. Here’s a roadmap to help you avoid these 7 ways to ruin a one on one:

Let it go on too long

When it comes to one on ones, longer is not better. At least past a certain point. You want to spend enough time with your report for them to fully discuss the items on their agenda, and for you to do the same. But since one on ones are done regularly (see below), these agendas should be relatively crisp after the first several weeks.

30 minutes should be plenty of time for a weekly one on one. There may be weeks where you need more time, but in general, if you are holding them regularly and working from agendas, a half hour should do it. Nothing will sap the energy and efficacy from a one on one like letting it roll on for hours. It’s like exercising – going for 7 hours one day is not as useful as going for an hour a day.

Keep them crisp.

Do it someplace with no privacy

The nature of one on one’s is that you will occasionally discuss items that are sensitive in nature. Some managers, in an effort to distinguish one on one meetings from project/status meetings (see below), will move the location to coffee shops or other places to help them feel more casual and promote better dialogue.

It comes from a good place – you want your direct reports to use the time for a free flow of information and making the meeting feel less formal can help with that. But if you go someplace like an office break room or coffee shop with no privacy, the employee may be (understandably) more reticent to share sensitive information.

Keeping it more casual than other regular meetings is great (get out from behind that desk), but just make sure it stays private enough for anything your employee might want to raise.

Don’t hold it regularly

There’s no way around this one. You need to have your one on one’s regularly. Allowing them to drop off your calendar some weeks sends the not-so-subtle message that these meetings are not really that important.

Your one on ones are an “A priority” meeting, or rather, should be. You can’t reasonably expect your employees to fully take part in these meetings unless you build trust and demonstrate that these meetings are important – in fact, they are among the most important things on your calendar.

No amount of proclaiming the importance of the meetings will overcome the action of not actually making them happen. Schedule them regularly and don’t cancel them unless you absolutely must. Expect the same of your direct reports.

Allow it to be interrupted

We’ve all done it; you’re in a meeting when some email, phone call or door knock interrupts with something urgent. During your one on one, unless it’s “the office is on fire” urgent, don’t give into the temptation.

Interruptions, like meeting cancellations, are a barometer of just how important the one on one meeting is. All the flowery speeches, emails and references to Harvard Business Review articles shared with your team extolling the importance of one on ones will not make up for the unmistakable messaging of allowing the meetings to be interrupted.

One on ones are the very definition of important but not urgent – make sure your actions match your rhetoric if you want your employees to fully buy in.

Weaponize it

This one should go without saying, but as my experience with my former boss attests, it doesn’t. No matter how good your reason, no matter how annoying your employee or how packed your calendar, you simply must resist the urge to weaponize the one on one by turning it into an attack.

This isn’t to say you can’t cover difficult subjects in a one on one; you can and should. But they should be framed to support the long-term growth of the employee and, by extension, the long-term value they can produce for the firm.

If you turn your one on one into a smackdown, you may as well give up on the one on ones altogether, because they will have been excised as an effective management tool in your arsenal.

Turn it into a status meeting

This is perhaps the most common foible I come across with my coaching clients. Happily, it is also easily addressable.

One on ones, with their focus on long-term growth and contribution, can be awkward and uncomfortable. Especially in the beginning. They are about building relationships between manager and report, and as such are a departure from the normal, transactional type of meetings folks are used to. I refer to these transactional meetings generically as “status meetings” or “project status meetings”. Your firm may call them case status meetings or something similar.

The key difference is, of course, that status meetings are about some project. They are logistical, strategic, and transactional – aimed toward helping the employee reach a satisfactory conclusion with some case or project. Status meetings are critically important to your firm – you’re not likely to get much done without them. But they are not one on one meetings, even if it is just two of you in the meeting.

One on ones are about the employee, their professional growth and contribution to the firm, and, more broadly, about the relationship between the employee and the manager. They are trust-building and focused on the big picture. They are not solving for small operational issues; they are solving for the bigger game of building a sustainable organization with an engaged team.

Keep the focus where it needs to be.

Make it about you

This last one is for the talkers out there. The extroverts. The chatty Cathies.

The final way to thoroughly ruin a one on one: make it all about you. I get it, I am a talker myself. Sometimes with the best of intentions, I am eager to make a connection or draw a common bond, and that eagerness just causes me to talk over the landscape. It’s a bad habit and it’s one I work on daily.

Your one on ones are like this, too. You’ve got to let them be at least 50% for the employee to discuss their agenda. Even if their agenda items seem less important than the ones on your agenda. Maybe especially then.

Remember, the one on ones are about the relationship. You are working on trust and communication. That is the goal, so make sure you keep your eyes on the prize and practice listening as much as talking.

Okay, now you have a map of all the pitfalls and trapdoors to avoid with your one on ones. Good luck with them – if you get them right, they can become one of the most rewarding parts of your firm management process.

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