“Decision-making is a mental muscle that teams have to build. When a problem comes up, your natural instinct is to say, ‘What’s the solution?’ But if you’re trying to build scalable teams, you have to insert this step of ‘How should we think about solving this problem? And then how can we systemize that so it can be used later?”
These words from James Everingham have stuck with us. In our view, this goal the co-founder of Lightspark and former Head of Engineering at Instagram lays out is the decisive organizational end-state every startup leader should aim for. But we’ll be the first to admit that the work it takes to get there isn’t easy. As a company scales from a handful to a dozen to hundreds or thousands of employees, it gets harder and harder to develop this decision-making muscle.
To build that system, it helps to start with sticking to a straightforward decision-making process — one that you can replicate and refine with every at bat. We’ve combed The Review archives to identify some of the more unique advice we’ve heard over the years, boiling it down into an easy-to-follow, 7-step decision-making process to help you overcome common organizational challenges and examine your choice from angles you might have otherwise overlooked.
1. Make sure you’ve outlined decision-making principles.
The first step in decision making starts well before you’re even facing a decision.
“A startup’s founding team uses a set of unwritten beliefs they all implicitly know and agree with to make hiring decisions and product decisions — but they never get said out loud or documented somewhere central,” says former Stripe COO Claire Hughes Johnson. “Do you know what these unspoken, unwritten things are? Have you categorized the common types of decisions you need to make? Have you documented the beliefs that guide how you make those decisions?”
This is where decision-making principles come in handy. “Establishing principles isn’t just about making decisions — it's making decisions that are well made, ones that you can explain how and why they were made” says James Everingham.
Keep it simple to start, with a slimmed down list of decision-making principles for your team to stick to. Everingham recommends choosing 3-5 that are high priority for your company. That’ll make it easier to actually integrate these new principles into your daily routine, and hopefully help cut down on decision fatigue.
Turn to other companies for inspiration. “We solve customer problems first,” is a decision-making principle that has stuck with Everingham since his days at Instagram. From her time scaling Stripe, Johnson saw the importance of making sure the principles were specific enough so that folks (even below the managerial level and below could use them to make the same decisions a founder would.
2. Decide how you’re going to decide by coming up with your decision criteria in advance.
“The worst time to make a decision is when you’re facing one down,” says Annie Duke. (Given that she’s a former poker pro and decision science expert, we’d trust her here.)
Restricting your thinking to the problem at hand can skew your judgment, making it too easy to let particularly promising — or less-than-promising — signals lead you astray. Say you’re interviewing a candidate with off-the-charts charisma. It’s easy to be swayed by this overconfidence, even if that’s not an important attribute for the role you’re trying to fill. Taking the time to outline which qualities matter most before you even sit down for an interview will help discipline your decision.
“Try thinking not about a specific decision in front of you, but the general decision space that you’re considering. Thinking about them before you’re actually facing down the decision will help you reduce the noise and the bias,” says Duke.
As an example, consider the decision to sell your company. Don’t wait to contemplate the question until you have an offer in front of you. As you’re building, try to unpack the circumstances that might motivate you to sell, the inputs you’d need to come to a decision, what an offer would ideally look like, the key players who would need to be involved, like a CFO or a well-constructed board.
3. Decide when you’re going to decide to avoid analysis paralysis and decision fatigue.
Time management may not be the first thing to come to mind here, but setting a deadline is an overlooked step of a decision-making process.
Dave Girouard, founder and CEO of Upstart, is a firm believer that the when matters much more than the what when it comes to decision making. In his classic “Speed as a Habit” article, he writes: “If, by way of habit, you consistently begin every decision-making process by considering how much time and effort that decision is worth, who needs to have input, and when you’ll have an answer, you'll have developed the first important muscle for speed.”
Deciding on when a decision will be made from the start is a profound, powerful change that will speed everything up.
4. Write it all down to create a decision-making record — and run through these questions to sharpen your thinking
As you move on to problem solving, you might have a “gut feeling” about a potential solution already in mind. Or you might be starting from a blank slate, with heaps of research, interviews and data to gather. Either way, it’s important to sit down and record your thinking as you weigh your options.
Whether you realize it or not, biases (like confirmation bias) and mental shortcuts (like the availability heuristic) can cloud your judgment. Your pre-existing preferences likely mean you've already started to arrive at a conclusion (which is why a traditional pros and cons list is not Duke's favorite — it risks amplifying the decision you were already heading toward).
There’s so much you’re taking into account, and without writing anything down, you’re leaving those assumptions implicit, which makes identifying mistakes and learning from previous choices even harder in the future, says Annie Duke. It also makes it more difficult to share your thinking with others and incorporate new perspectives.
To make great decisions, you need accountability, repeatability, and examinability. I always describe it like this: We need to create an evidentiary record, a way to Google our own decision-making.
If you’re looking to create a more robust record, here’s another resource: When ex-Amazon leader Kintan Brahmbhatt is wrestling with a particularly weighty decision or significant strategic change, he ticks through this list of questions to pressure test his thinking:
- Why now?
- Is this a reversible or an irreversible decision?
- If irreversible, what makes it so? Can I break it down into multiple smaller decisions, some of which may be reversible?
- What factors won’t change in 10 years? How much of our plan is optimizing for durable traits versus betting on new trends and traits that will change?
- How do we know we are succeeding in our goal?
- What are the top controllable factors that impact the outcome of this decision? Have I focused on them appropriately?
- What are the top uncontrollable factors? How am I mitigating their risk?
- What is the worst-case scenario? What concrete steps can we take to ensure that the worst-case scenario does not happen? What steps can we take to rebuild, should we hit the worst-case scenario?
5. Schedule a meeting, circulate your pre-reads — but don’t let groupthink get in the way.
As Duke mentioned above, with your own thinking more crisply captured, it’s easier to share and get the perspectives of your teammates. But there’s an art to bringing others in. The decision-making kitchen can get crowded with too many cooks very quickly. But involve too few, and there may be glaring blindspots that you end up missing.
If you’re adding a big decision point to the team meeting agenda, we’ve curated some tactical pointers that will help you keep these discussions on track, evaluate new ideas and avoid decision fatigue.
Superhuman founder and CEO Rahul Vohra uses two formats here:
- Issue: “This is less than half a page and includes a 1-2 sentence description of the problem, and super importantly, a 1-2 sentence description of your intended solution. The ideal flow in the staff meeting is the person proposing the issue and solution asks, ‘Does anyone disagree with my solution?’ and if no one does we can move on, and it’s a 30-second discussion. With more junior staff teams they’ll bring a problem, but they’re not holding themselves to the bar of bringing a solution — that part’s really important.”
- RAPID: “For thornier decisions, we follow the traditional RAPID framework — listing the problem we’re trying to solve, the proposed solution, the owners, input from others, and the final decisions.”
But what’s most unique is his strict rule for executive team meetings: “If you have not read and commented on the document beforehand, you’re not allowed to talk about the topic in the meeting,” he says. Before implementing this rule, decision meetings would drag on, hurting productivity and slowing things down as too much time was spent just recapping the problem. As a consequence, there wasn't enough space to discuss solutions.
Annie Duke, unsurprisingly, is concerned with how cognitive bias can affect these team decision meetings. It’s important to gain team member insights, but only if your own leanings don’t influence this input. That’s why she recommends collecting decision feedback and brainstorming ideas independently and asynchronously — to avoid "infecting" the group. Here’s a few simple approaches as you gather outside perspectives:
- Have team members write down their opinions anonymously on a virtual whiteboard. Or if in person, have them write it on a piece of paper to pass along so someone else can read their take.
- If folks on your team are sharing their own opinions aloud, go in reverse order of seniority.
- When sending an email asking for feedback on an idea, ask everyone to email you directly instead of replying all. Then aggregate the results and share out.
6. Head off risks and make use of pre-mortems to catch mistakes before they happen.
Most of the handwringing, indecision, and lost sleep for decision makers stems from all the ways things could go sideways — the risks, the faulty assumptions, the execution errors that you didn’t see coming. By following a standard, yet thorough, process for poking holes in solutions, you can calm your nerves — and timebox them too, so you don’t spiral in anxiety over potential pitfalls. These two heuristics are particularly useful in a startup setting:
Think holistically and focus on mitigating risks.
Thirty Madison CTO Gil Shklarski developed an immensely useful decision matrix while he was at Flatiron Health, one that his teammates dubbed the “Xanax for decision-making.” It might appear to be a simple pro con list, but the “Mitigations” row is the special sauce here. (This particular example involves the choice to introduce titles and leveling at the company.)
Consider the ripple effects of a decision. Flex those emotional intelligence and management skills by trying to identify the team dynamics at play, not just the more obvious outcomes. “For example: Will a manager be made happy by a certain decision? Will a team be energized? Will someone who deserves visibility in the organization be given an opportunity? As the company grows, how will these impacts change?”
Run pre-mortems, not just post-mortems
We're a fan of this heuristic from Persona co-founder Rick Song: “Oftentimes the question of why something won’t work uncovers the element that actually does make it work. ‘Why would a customer not want this?’ is often a far more interesting question than why they would."
To dig even deeper here, you can try out this framing from another founder, Mutiny’s Jaleh Rezaei. Her “black hat technique” requires managers to ask their teams a tough question: “Let’s assume that it’s one year from now and we’ve failed at our goal. What went wrong?”
Try to list 5-10 implicit assumptions about what would derail your success, and then turn these negatives into positives — the levers you can pull on to make things work. These are the assumptions that must be true in order for you to succeed.
7. Disagree and commit, then circulate
“Good” decisions still need explanation, especially if they weren’t unanimous. Articulate your rational thinking, making it clear in your reasoning that you understand your decision’s impact and own whatever comes as a result of that choice.
Square’s Gokul Rajaram developed the SPADE decision-making framework: setting, people, alternatives, decision, explanation. During this final step, he recommends hosting a commitment meeting where you're decisive and ask each team member, one by one, to support the choice. “Commitment meetings are really important, because when you pledge to support a decision in the presence of your peers, you're much more likely to support it.”
Then, it’s time to circulate. “The decision maker should email the brief to the rest of the company or to as broad of an audience as possible. Why? Because the company needs to be informed of what and how decisions are being made. Square used an email alias (notes@) to send all kinds of decision and meeting notes around.”
8. Set kill criteria so you know when to quit a decision
This is another oft-overlooked decision-making step. Whether it’s sunk cost fallacy or status quo bias, we all have a bias toward sticking with our choices — founders and startup leaders especially.
If you’re looking to build in off-ramps from the start, set up what Duke calls “kill criteria” — the benchmarks that will cause you to reverse course or shutter a project when you miss them. “Use ‘states and dates,” she says. “‘If by (date), I have/haven’t (reached a particular state), I’ll quit.’” To make them most effective, evaluate these guardrails regularly with an investor or external advisor to help push back against your natural tendency to grit your way through.
9. Review your decision’s impact — the good with the bad
As you consider previous choices, don’t just assess the results. Try to trace back to what you knew before you made it. What was revealed after the fact? Could you have known about it beforehand?”
You can learn just as much from evaluating decisions that went well as you can from those that didn’t go as expected. As Annie Duke notes, we tend to probe for the root cause of only the bad outcomes, like missing sales targets — not exceeding them, even though that’s also a signal that something didn’t go according to plan. “Examining only one side of the equation not only causes you to miss out on half of your opportunities to improve your decision making.”
Startup life is equal parts scary and stressful, but the rewards are often well worth the investment (literally and figuratively). To discover more ways you can fine-tune your leadership skills, check out our article on the25 micro-habits of high-impact managers or read abouthow to audit advice so it’s valuable and not overwhelming.