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5 Things I’ve Learned About Leadership Working With a New Assistant

That’s natural, but I had to be very careful not to project that on my new assistant (or others).

I actually felt quite a bit of internal resistance to all the changes that were taking place during the first month or two. (The irony was not lost on me since I wrote a book about overcoming opposition to organizational change.)

But I soon saw that not letting go of the past is the first, sad step toward living in the past. And I’ve seen so many leaders do that, to everyone’s detriment.

If you want to embrace the future, you’ve got to let go of the past, no matter how much you may have enjoyed it.

And ironically, once you do, you’ll see how awesome the present is and how good the future can be.

2. Ambiguity is a terrible training manual

One key to an easy transition is to have your systems and methodology written down.

I’ve done a decent job of writing down the mission, vision, strategy and culture of Connexus Church, where I serve. (I outline how I did that here.)

My new assistant Sara’s main job is not to help me with the church side of my life, but with this blog, with my leadership podcast, with my speaking engagements and the rest of my life. Those things have grown exponentially over the last few years, but I’d never made the time to write down the mission, vision, strategy or even culture I’m trying to embody in those areas.

That makes training someone new much more difficult. Ambiguity is a terrible training manual.

This kind of ambiguity almost always results in a leader telling a new team member what’s wrong, not what’s right. The dialogue can almost end up sounding like this:

No, I don’t think that’s right.

OK, well let me try it this way, is this better?

No, that’s not it either.

How about this?

Um…not really.

Well, can you help me understand what you’re shooting for?

I’m not 100 percent sure actually.

Fortunately for me, my new assistant Sara is sharp and we avoided countless rounds and rounds of this.

We actually found a groove on culture, communication and process faster than we might have largely because she is really good at reading between the lines and is highly motivated to get there fast.

But the process has taught me I need to codify as much as I can quickly.

You can’t scale ambiguity.

3. Reasonable expectations are your friend

Like many leaders, I am an optimist.

And so I regularly underestimate how much time things take, how many bumps there will be, and I often assume everything that’s unreasonable is reasonable.

In many ways, that’s a strength, but it’s also far healthier to have reasonable expectations and timeframes in place.

Underestimating the challenges in front of you only creates new challenges.

There will be a transition period with any change. And as a leader, you need to make time for it.

If I was guilty of anything in the first 60 days, it was probably that I kept assuming the transition was ending, when in fact, it was perfectly normal to still be in transition.

Ironically, if you plan on a transition, the transition period will end sooner than if you pretend there’s no transition.