3 Things Great Leaders Know About Timing

“I’ll help you with the event,” my good friend says. Then he never shows up for a meeting. You probably know who my good friends are anyways. If I didn’t care about this, I’d just say who it is.

But I do. Care, that is.

I’m writing this after three hours of sleep. In case you want to run an event or startup, here are a few things to keep in mind.

Timing is everything1. Remember what they say about mixing business with pleasure.

His girlfriend starts helping us, then he doesn’t let us recruit any of his friends. Isn’t your trusty best friend supposed to arrive when you dial the bat mobile? Okay, I may have the wrong number because I haven’t actually seen the Dark Knight.

What am I doing with my life that one of my best friends can’t keep a simple promise?

You can be friends with people you work with. But you don’t necessarily want to work with your friends unless you can risk losing them. Like, I don’t mind working with batman because I don’t know him, but he’s supposedly a hard worker with great biceps.

Maybe we all have friends we can’t work with, no matter how talented they are.


2. Learn about the team.

Pop culture says INFP personality types are not poised to be managers because we are so consumed with keeping peace that we tend to place achievement of team objectives below maintaining a great team dynamic.

I want to say that’s not true, but I’m like the reverse customer service desk. I will call to make sure you’re okay with your role and I will put myself on hold and even sing my own elevator muzak until you’re done meetings or cooking or whatever you want to do besides speak to me (crazy, right?).

When planning the timeline, we didn’t account for the month of fire-up time for settling into team roles; that is, how long the norming stage of team formation was. We lost more than a month that way.

Around this time of year, music teachers are growing their businesses and hiring new instructors.

You will meet people who are committed, and also people who are interested in what you are doing, without the same dedication. Ask them for favours like contact lists and introductions; ask for everything you think they can help with and let them say “no.”

We all know that “no” just means “no for now.”


3. Make defining decisions.

We only hired people in our circle because we wanted to get started as quickly as possible. We were small and agile but could’ve used more manpower at times, like when we wanted to call every tech company in the city.

I’ve been reading leadership and management literature lately; Badaracco’s framework for making difficult decisions, in Defining Moments, makes a lot of sense to me.

In a nutshell: when faced with a difficult decision, find the middle ground and don’t piss anyone off.

Let’s say you’re a piano teacher at a prestigious conservatory. You plan to teach at a different conservatory in the coming months, and your managers have asked you to keep this quiet for now.

One of your lovely students, Jenna, is serious about pursuing music, and has enormous potential.

Her parents say they plan to place a down-payment on a home near your conservatory because she wants lessons with you specifically. They ask whether you will stay at the conservatory long-term; if so, they are placing the down-payment next week. If not, there is another home by Jenna’s high school, that happens to be close to the new conservatory you’re moving to.

Do you tell them you’re leaving?

It is right to prioritize the community aspect by telling them you are moving, because you want to help them make a favourable decision when purchasing a home. It is also right to prioritize the individual aspect by keeping it a secret, because your managers have asked you to do so and your career is attached to thisyou’ll be in trouble if all of your students quit.

When speaking with the parents, you might discuss how you think the housing market is more favourable on the other side of town. You might recommend trying different teachers’ instruction styles. You might point out that university music programs look for versatile musicians and recommend some jazz.

You can say anything to hint at not placing the down-payment as long as you don’t mention you are leaving.

You are making a middle-ground decision using Aristotle’s Golden Mean to avoid pissing anyone off, and you’re playing Machiavelli’s fox as a strategy–Badarraco applies philosophers’ ideas to daily life and I love that. See? Wiser already.


I am still sad once in a while. I’d like to say it gets easier everyday, but that’s not exactly how it works. Some days are good, some days I am torn.

Beyond that, I am determined. If I have to grind everyday to get this event off the ground, then I will do so. If you are working on something you care about, maybe it doesn’t get easier, but it gets more satisfying.

Now that I am on the topic of grinding, I might as well say this – if you are part of a tech or health company that might be interested in sponsoring a health hackathon (recruit talent, be the first to see great technology) where 300 people find ways to improve a cancer patient’s life using software/hardware/3D printing, shoot me an email at contact[at]designlablive.com. We are always looking for new partnerships.

Because, you have to eat your words, you know?

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