Ask the Strategist: Rules for Collaborating with Driven People

Harvest Zau Marsh

“Ask the Strategist” tackles your questions about productivity, operations, decision making, and results.

Hey Sebastian –

One of my most persistent collaboration issues is working with forceful, headstrong personalities. A powerful, long-term drive can simultaneously create a deep and innovative subject matter expert as well as a deeply entrenched viewpoint and working style.

As a technical worker, it’s hard for me to route around these technical forces of nature, but I’ve also had a hard time effectively navigating a collaborative relationship. Have you found any effective communication/collaboration strategies for this case?

— Chad W.

A fine question, Chad. I feel rather qualified to answer it — both because I have some great collaborations with a number of people like that, and additionally — I’m sometimes in that “forceful and headstrong”  category myself, so I can explain what it feels like on the inside.

I see three keys to working with very driven and forceful personalities:

  1. Respect the universals of working with people.
  2. Manage both information and affect.
  3. Keep the focus on outcomes.

We’ll go through each of them.

1. Respect the universals of working with people.

The first universal rule I have is this: “You can’t do good business with bad people.

No matter how talented, brilliant, creative, expansive, or whatever else someone brings to the table, if the person is fundamentally mean-spirited, cruel, lacks integrity, or any such thing — pass.

Violate this rule at your peril. It can be very tempting to hire someone who is brilliant but ethically challenged if you badly need to fill a role, or take on a client who treats their staff poorly if you need cash, or to partner with someone who seems like they’ll get you to the next level in spite of that “warning sense” going off.

Here’s my advice — don’t do it. The old yarn, “Judge talent at its best and character at its worst” rings very true to me. If you see signs of problems in someone’s character and fundamental way of doing things, move on. A lot of amazing people have idiosyncrasies, which is fine if they’re well-meaning and fundamentally solid. But no clever strategies can manage things like dishonesty or meanness in a person; pass if you see any of that on a character level.

My second rule is: “Only work with people I admire tremendously.

Anyone who does any sort of freelancing, consulting, or sells a service will start to recognize the hallmarks of a bad client very early. You can tell right away — and savvy people filter them out.

But I recommend going a step further: only work with people you tremendously admire.

When there’s a genuine mutual admiration between people, it smooths so many potential problems out. All kinds of petty issues just simply don’t come up when each person feels really honored and privileged to be working together.

My test, by the way, for if I like someone enough to work with them — I ask, “If I worked nonstop with this person 10 days in a row, 16 hours a day… would I want to hang with them for three days on the beach afterwards to decompress and recharge?

That’s a pretty tough bar to clear, when you think about it. If you put in 160 hours over 10 days with someone, you’re probably sick of them and don’t want to be around them, regardless of how great they are, right?

But it’s a great glue when you genuinely like being around someone a lot, and admire them. I can work a month straight with Kai Zau on something very intense, and then hop on a no-internet long trip with him to recharge, and it’s marvelous. There’s not many people like that. Search them out, find them, work with them, and your life becomes marvelous.

The third rule is this: “The only way to build great relationships (including business relationships) is to eat salt together over time.

In Aristotle’s Nichomachean Ethics, he wrote that “men cannot know each other till they have ‘eaten salt together’; nor can they admit each other to friendship or be friends till each has been found lovable and been trusted by each other… a wish for friendship may arise quickly, but friendship does not.”

No matter how much you respect and like someone, great business ties  only come from a mix of time and going through strife together.

I always recommend against quickly becoming full business partners with someone in an enterprise if you haven’t worked with them. Instead, look to have “project partners” where you commit to doing a relatively small, scoped project and see how each other’s work styles are, and how you really fit together.

One of the biggest things that kills startups is cofounders falling out. Wouldn’t it be better if you’d already done 3, 5, or 10 small projects with someone before fully getting into business with them? It de-risks working on larger projects tremendously, and you get to see character flaws when the stakes are a lot lower.

Even things as a small as joining planning and running a dinner, salon, or small event goes long way towards getting to know what someone is made of.

2. Manage both information and affect.

So you’ve got your universals in place — the person you’re working with has solid character, you really admire and like spending time with them, and you’ve proven you can work well together through smaller-scale collaborations.

And yet, they’ve still got a personality that’s forceful, intense, idiosyncratic… how do you manage this?

This is where I like to consider the divide between managing information and managing affect.

A lot of very talented and creative people run on morale and esprit d’corps… they can run out an immense amount of work very quickly when inspired and in a great flow, but the sometimes haphazard nature of wild super-productivity can be hard to work with.

This is where I come down to breaking apart information and affect and thinking about both of them.

If you’re the more operationally-inclined person in a creative partnership, you’ll be trying to do things like setting a clear scope, ensure to-do lists are maintained and done, keep work focused, etc.

It’s critical that, while you do this, you also think about managing affect.

“Affect” is the emotion, the momentum, the feel of things.

I see a lot of operationally-inclined people get this wrong.

It’s critical to set scope and manage the information and general work, but you wouldn’t choose to work with someone who is forceful and intense and creative if you didn’t think that style led to outperformance in some way.

So the question for the operationalist becomes: how do I keep the information going while setting a positive and good affect and keeping morale and momentum high?

A classical example is a brilliant salesperson and a sales manager. The sales manager wants the salesperson to fill in the CRM software with all the data, keep good metrics, follow best practices. The brilliant salesperson, meanwhile, mostly just wants to sell and not be distracted.

Your challenge, if you’re on the operational side of the coin, is how you manage to make the CRM either painless and automatic to do (for instance, setting up Auto-BCC so that copies of all outgoing emails are automatically sent to the CRM without friction and without thinking about it), or otherwise make the metrics feel good to input and work with.

I’ve had clients and partners that just simply don’t want to do this. It’s a challenge and takes time to show and feel how powerful it can be when you keep good records, keep metrics, and flesh them out into week-by-week progress on sales, revenues, etc.

But again, if you’re asking from the point of view you’re asking from, you’re probably on managing the information adequately already — the big challenge becomes how you keep the morale, momentum, and excitement while doing it. Most people dislike doing admin, and those forceful and headstrong brilliant people often dislike it the most… the challenge becomes how you can navigate the feelings around that so it doesn’t feel like you’re bogging down key outcomes.

It’s not always easy and it’s very personal, but that’s the big thing to think about: how you’re re keep the mundane and routine from feeling like a drag and busting up morale.

Which brings us to the third point —

3.Keep the focus on outcomes.

You want to focus on outcomes instead of personality or little squabbles besides the outcomes.

It’s often obvious how really intense creative people need to ensure they’re working on the right things — and we’ll get to that in a moment — but let’s start by ensuring that you’re not getting in the way of great outcomes by insisting on process or uniformity.

Let’s take a look at the excellent company culture document called the “Genius-isms” from which my friend (and brilliant operationalist) Taylor Pearson showed to me.

One of their rules is “The Chaos Will Not Be Minimized” —

“Building anything great is messy, and Genius is no exception. We are pursuing a results-maximizing strategy, not a chaos-minimization or comfort-maximization strategy.

It can be comforting to insist on buttoning everything down, but if you’re in a fast-moving space, you need to ask if insisting on uniformity and cleaning everything up is really the way to maximize outcomes.

It might be — but it also might be you trying to make yourself more comfortable at the expense of outcomes. If you signed up for working with a partner who has some Steve Jobs type attributes about them, you signed up for some chaos — and a whole lot of results.

So before you insist on everyone getting receipts very carefully for expenses, you might ask if that’s really serving the enterprise’s goals. Maybe it’s better to let things be a little loose and crazy right now, if everyone is working hard and discretionary expenses aren’t out of control.

So — if you’re playing the “responsible adult” role in the business relationship, make sure that whatever you insist on is really worth it. You need some structure and process, yes, but you need to not kill off your productivity in the process.

The flipside of this, of course, is getting the wild and creative person in the business relationship to ensure that they’re doing what makes sense for the business, as opposed to just working in a manic frenzy.

How do you do that?

The answer here is pretty mundane: best practices and regularly asking, “What are we trying to do here?” and discussing and updating it periodically.

I’ve seen some teams successfully “lock” the work to be done for a particular sprint, and refuse to revisit it until that work is done — potentially quite useful if you’re going in too many directions at once.

As a small tip that’s really very valuable, I recommend that whoever is busier and less organized write the agenda for meetings.

It’s counterintuitive, but generally speaking, the more organized person will buy-in to the agenda, and the less organized person… might not.

By having whoever is busier and less organized write the agenda, they’re then much more likely to respect it and actually turn those into agreed targets to hit, which then become the outcomes you manage by.

And on a final counterintuitive note — I find the best ops people are the ones who are flexible as to what tools and mediums of communications they use.

Similar to how Bruce Lee said that the best style is no style, I find the more organized and responsible person in a business relationship is better off adapting to the preferred software, communication style, and meetings style.

I’ve been on both sides of that fence — I’ve been both the more organized and less organized person — and you definitely get both higher adherence and more goodwill if you spend time finding the tools that are the right fit for the current project or enterprise instead of trying to shoe-horn your preferred tools.

This takes some learning, experimentation, and flexibility — but it pays off in spades.

So again,

  1. Respect the universals of working with people.
  2. Manage both information and affect.
  3. Keep the focus on outcomes.

And godspeed in your creative collaborations.

Sebastian Marshall

Got a question for “Ask the Strategist”? You can write to Sebastian at

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