Never Have a Tough Conversation Over Email. And A Few Other Unforced Management Errors.

So perhaps the best management advice you’ll hear again and again is this:

#1. Never Have a Tough Conversation Over Email

Yes, you probably know this. As tempting as it may be to avoid conflict, headaches, and hearing things you don’t want to hear — never have a tough “conversation” over email.

And yet, most of us only half listen. And these days, when almost all of us run distributed teams, this advice is ignored again and again. We’re all so used to communicating all day on Zoom and Slack … that why shouldn’t tough news be delivered that way?

Well, the reason is there is almost 100% chance it will be misinterpreted. And there’s zero chance to inject any human element into things.

Now, there are a few exceptions. If you have to fire someone for clear issues, email is probably a better way to do it. It makes sure the problematic employee knows for sure the relationship is over.

But a few unforced errors here:

• Changing someone’s role over email that you want to keep
• Quitting over email if you want a positive reference or any positive benefits from your time there
• Providing criticism up or down the chain over email. It can be a good place to frame a conversation you are having. But almost no one responds positively to rough feedback only over email.

The bottom line is email “conversations” are ripe to be interpreted in the most negative of ways. And they can break relationships instantly — that were never intended to be broken. Be careful.

You can take back almost anything said in person, at least in a business context. But it’s really, really hard to take back an email. Almost impossible.

And a few other basic Unforced Management Errors — that we all still make. Including me. At least be aware of them, and break these rules intentionally.

#2. Slow Down Big Decisions. Speed Up The Rest.

This saying is one of my favorite ones for fast-paced start-ups. There are so, so many decisions to make as founders. Too many, really. So 95% of them you have to make right now, today. Don’t put them off. Then instead of 10 problems, you have 20, then 100, and so on. Speed up all but the biggest decisions. And especially — speed up any that are reversible, and have a good manager to manage them.

But too many founders (including myself) take this a step too far and also speed up big decisions. The make or break ones:

• Should we sell our company? Take your time. Not forever, but if you need more time, just take it.
• Should we do that too aggressive marketing campaign? That maybe crosses the line? Sometimes. But put it back in the over for a week.
• Should we raise prices on all our existing customers? Most of you did last year. But it has a cost.
• Are we sure that’s the right lead investor?
• Are we sure we should increase the burn rate?
• Are we sure we should hire that VP of Sales, that we’re not 100% sure about?

There’s probably 1 decision a quarter, maybe 2, that you should slow down. The rest, speed up.

#3. Have Some Form Of 1-on-1s With All Your Direct Reports. But They Don’t Have to Be Formal 1-on-1s.

Too many of us have stopped, or never have done, weekly or at least bi-weekly one-on-ones with our direct reports. We tell ourselves it’s because we’re too busy. We tell ourselves now that we do daily stand ups on Zoom, why do we need yet another weekly meeting? And we also, in a distributed world, tend to hide from interacting folks we don’t want to interact with more than we used to.

But you gotta do your 1-on-1s for your direct reports. If it’s too many meetings, that likely just means you have too many direct reports. Every week is best, but every other week is OK.

I know sometimes you don’t want to do them with VPs you don’t quite believe in, or that aren’t your top performers. Too bad. They need the most help of all. And doing the 1-on-1s will also push you to upgrade that position sooner.

And I know sometimes you don’t want to do 1-on-1s with your top performers because they just plain execute. You want to lean on them more, and keep your schedule free. But they need you even more. Not for help doing their job. But to know someone has their back. And importantly, to each week or two, talk through the tough issues on their mind. Again, with your top performers, they don’t have to be formal 1-on-1’s. But you gotta make the time to catch up with them.

The very best get lonely. There’s no one to talk to about their jobs, even if they have a big team. That’s part of your job for your top performers in your 1-on-1’s.