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A Guide To Co-Leadership: Why It’s Hard, Why It’s Good, And How To Make It Work

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Editor’s note: Aaron Schildkrout is a New York City entrepreneur and product thinker. He co-founded HowAboutWe.com (acquired by IAC, 2014) where, as co-CEO, he oversaw product development, design, data, and engineering.

In September Larry Ellison stepped down from the helm at Oracle and appointed a co-CEO pair as his successors. Articles about the announcement spoke of such dual arrangements in discouraging and doubtful tones.

Meanwhile, in NYC, a well-regarded VC recently told me that she thought at least 50 percent of early-stage startup failures are rooted in co-founder conflicts. 

And this a few weeks ago from Pando.

Not surprising. In a time when collaboration is a flourishing ideal, shared leadership is an increasingly attractive proposition. And yet, leaders are the fulcrum that receives, holds and either utilizes or gets crushed by the considerable pressures generated by early-stage company building; two is not necessarily better than one at the cornerstone. 

Said otherwise: multiple founders/CEOs means more complexity, and while more complexity at the fulcrum can mean more strength (internal levers, combustion systems, failovers, etc.) it can also mean considerably more vulnerability to fissures, conflict and collapse.

This post is a brief guide to co-leading. I’ll outline why having co-leaders is hard, why it’s a source of enhanced productivity, creativity, and joy when it works, and some tactics for success. 

I’m going to use the term co-leading throughout. I’m focused primarily on co-CEO relationships, but I think what I write applies equally to co-founders and other collaborative executive structures.

I’m writing primarily from my experience co-founding and subsequently co-CEO’ing HowAboutWe with Brian Schechter, my best friend since childhood. Over about five years, we grew the company to 100 people, and then — this past summer — sold it to IAC. We’re still best friends.

Why It’s Hard

The company is the body of its leaders.

Everything is on you as leader: both superficially, in that your work ethic, smarts, creativity, values, vision, etc. will determine the path and success of your company; and also fundamentally, in that your company will look, feel and operate in accord with your actual constitution. 

This is true in a long-term sense (you will reap what you sow) and in a short-term sense (if you’re enthusiastic today the company will feel up; if you’re down people will be miserable).

This translates into huge pressure on co-leaders and their collaborative relationship.

Each weakness in your co-leaders will diminish your own chances of success. More subtly, everything your co-leaders do will be a reflection on you; and so their weaknesses become your weaknesses in the public eye. Conversely, your weaknesses (yes, you have them) will become deeply known – and very possibly resented  —  by the people with whom you’re leading. 

Most frequently, the fissures manifest in the process of setting and executing on your company’s core strategy. Here’s why… 

First, and most obviously, your strategy will determine your company’s fate  —  so the stakes of consensus are high.

Second, different people approach strategic questions in accord with their natures (e.g. Bill’s a cynic, so he sees the potential pitfalls as more likely than the next guy and so chooses a more defensive strategic position than Jane, the optimist). And so, in your strategic debates you are actually debating your fundamental world views; whether or not you are psychologically oriented enough to see and state this, it will be felt.

Third, co-leaders often take more extreme positions in strategy debates than they would were they solo at the helm. For one thing, they know that their co-leader will balance their extremism. Also, an extreme early position in a strategy debate can be used later as retroactive rationale for why we “should have done it my way.” Yes, this is all rather embarrassing, but the psyche is the psyche. This extremism can dilute rationality and lead to pigeonholing and blame. 

Fourth   and most important: Setting core company strategy is where co-leaders often run into the biggest accountability challenges. As co-leaders, you have so much to do that you absolutely must divide and conquer. And yet, you often have to do this in areas where boundaries of responsibility aren’t totally clear. Roles, titles, and agreed-upon purview only go so far. The rub: If more than one person is equally in charge of something it is incredibly difficult to avoid subtly relinquishing responsibility and accountability. Hard decisions can become harder to make. And your company becomes at risk of a pleasant mediocrity.

Alas, the challenges of co-leading don’t stop there…

Comportment! You are the chief bards for the company  —  telling the company story and defining the brand in the way you comport yourself all day every day. Alignment is essential and difficult to attain, particularly as the company story evolves. 

Money! Equity- and finance-related issues can be particularly complex, forcing co-leaders to agree on their relative importance to the company  — both historically and going forward. 

Mood! It’s not like the conditions are easy. Things are moving very quickly. Time and energy are precious commodities. You have big problems to solve. You are stressed and haven’t had an eight-hour night of sleep in months. It’s hard to stay hydrated, let alone well-rested, let alone pleasant company.

And all of this is glaringly visible to all. The public nature of your relationship makes challenges exponentially more difficult to mediate. 

So it’s not surprising that co-leader relationships can easily degrade into a Petri dish for any number of pathologies: cycles of blame, guilt, and shame; self-perpetuating patterns of anger, frustration, defensiveness, poor communication, misunderstanding; and so on. It can get ugly. It often does.

And if you succumb to this it will genuinely hurt your company’s outlook.

But It’s Important…

And yet, two can be exponentially more powerful than one.

Co-leadership can be an extremely powerful lever for building a great company. Indeed, it can and should be energizing, efficient and inspiring for you, your team and your company. Why?

  • Smart collaboration among leaders results in more creative, better-vetted, more strategic solutions.
  • A group will have more strengths — categorically — than an individual. If you know how to help each other lean into these individual strengths, you can build a powerful, well-rounded core.
  • Multiple leaders means more wells of positivity and motivation to tap. The best co-leaders build a rotational system of sorts that allows each person critical periods of rest and replenishment.
  • Co-leaders can build for each other a genuinely safe sounding board for bad ideas — a necessary purification process to arrive at the precious great ones.
  • A hundred business cases call for some duality from leadership: good cop / bad cop; theoretician / pragmatist; optimist / skeptic; and so on. Great co-leadership relationships consciously allow these dualities to manifest in ways that aren’t fundamentally conflictual.
  • Psychologically, you can alleviate for each other, to a degree, the peculiar isolation and other challenges of executive roles. And inversely, you can genuinely support each other to grow in the difficult but enlightening ways demanded by the role.
  • You can much more effectively manage growth with multiple founders/leaders, adding stability to the somewhat inevitable chaos of going from 2 to 10 to 20 to 50 to 100 to 500 people, and onward.
  • The experience of friendship with your co-leaders can be rich, gratifying and illuminating. You can — and should — have a blast building your company together. The energy that comes from this will be apparent and elevate your whole team. 

And so on. The boons of the collaborative leadership assuredly make the challenges worth traversing.

So, How Do You Do It?

Here’s my top 5 list, plus a bonus track:

1. Pick the right people. This one is obvious but critical. Regarding the people you co-lead a company with, be sure the relationship fulfills these three requirements, at an absolute minimum:

  • Trust (in their values, ethics and rationality)
  • Genuine admiration (of their talents as lever-moving for the company)
  • Effective and inspiring collaboration (particularly in high-pressure, complex conditions)

2. Expect conflict and build structures to address it consistently and systematically. This one is so easily overlooked amidst the excitement of creation, the contagious feeling of invincibility, and so forth. Don’t miss this. If you aren’t running into conflict, you likely aren’t pushing your limits enough. Conflict isn’t bad; it is a common side effect of drawing out each person’s unique perspective. You need to create a consistent system for reflecting on your co-founder relationship: what’s working, what’s failing, how you can improve, etc. Calling on outside support to facilitate this is often a good idea.

3. Define very clear roles and responsibilities. Again, so obvious but so easily screwed up. Ninety percent of the division is really easy. It’s the 10 percent that will get you. 

This 10 percent includes, most importantly, areas of shared decision-making. I would say you should almost always choose being left out over sharing accountability. Without extremely refined skill, shared accountability means less accountability. If you share responsibility you will end up relinquishing it in subtle and damaging ways. Each thing should ultimately be owned by one person, even the most mission critical things. You have to trust each other.

The 10% also includes tricky issues that traverse various areas. A classic one here is data. Data often is the responsibility of marketing and product and sales. But who really owns it? You need to proactively, and on a granular basis, get really clear about who owns these category-traversing business functions.

4. Speak in percentages. About a year into my co-founder/CEO relationship with Brian, we realized that we kept getting into conflicts around issues that we actually agreed on. I had a tendency to say that things with small likelihoods had “absolutely zero f@#$!#$ chance of ever working,” while Brian tended to embrace the language of possibility: “that definitely could work ☺!!” Turns out we both thought the thing in question had about a 17 percent chance of working. Upon realizing this, we started avoiding all vague probability terms and talking in actual percentages. Doing this eliminated about 40 percent of our conflicts.

So, “speak in percentages” is my way of saying: Find the communication techniques that help you arrive at understanding, consensus and useful action. 

5. Know your own weaknesses. If you are incapable of seeing your weaknesses  — and particularly the things you do that are hard for your co-leaders, even if they aren’t categorically counterproductive — then you will end up in a prideful, defensive, unhelpful stance. If you see your weaknesses then you will be able to build a balanced view of the relationship dynamics that will support rapid de-escalation and effective collaboration. Your vulnerability will be fuel. Any time you spend being defensive is time wasted. 

Bonus Track: Don’t forget to be funny. Humor is the most unsung of all leadership skills. If you don’t laugh your asses off pretty frequently then you are probably in for trouble. I’d say this is a subcategory of the bigger necessity for fun and friendship. You don’t need to go drinking every night together. But you should spend time together, laughing at the absurdity and excitement of the whole endeavor.

We are in a collaborative moment. As such, I imagine that collaborative leadership will become increasingly common  — and hopefully we’ll also become increasingly skilled at making these relationships truly work. 

Because, when they do work — which is to say when you make them work — you unlock a groundswell of productivity, intelligence and inspiration.