In my early 30s, a group of executives decided to overhaul the strategic direction of my team, and I wasn’t even in the room. One day, my team was working on a certain project, and the next, we were working on something else.
I was a trusted manager and engineer. I’d built a great team that had shipped a bunch of hits. And I had plenty of ideas. So why wasn’t I at that meeting? It stung. But now I know one reason I wasn’t included is that I just wasn’t providing the type of strategic thinking that the execs needed to make a decision.
Many believe that being strategic is a talent that some people have, and some don’t. Natural ability is certainly one component, but I’ve found through my own experience and through coaching others that being strategic is a skill that can be learned. But first you have to figure out what’s getting in your way.
Numbers: ‘Who cares?’
When Redfin’s CEO, Glenn Kelman, was in his early 20s, he attended a board meeting where he was asked for a number that he didn’t know off the top of his head. Instead of saying, “I don’t know,” he gave what he thought was the right number and was immediately corrected by someone else in the room. Your credibility is your only currency in business, and he’d lost it in an instant.
When preparing me to attend my first board meeting at Redfin, Glenn told me this cautionary tale and said he’s now careful to start every answer to a board question with “yes,” “no,” a number or “I don’t know.”
Starting your answer any other way will sound evasive rather than crisp. And if you don’t know the numbers, you’ll end up saying “I don’t know” a lot.
Your top priority is to start worrying about the high-level numbers that your executive team worries about. If you can’t connect your ideas to a better customer experience, revenue, or profit, then it’s unlikely that you will be considered strategic.
Most companies have an important document or a video where the CEO explains the high-level strategy and numbers. If you can’t find it, ask for it.
Next, recognize that an executive team is surrounded by people who have an agenda that has nothing to do with these numbers. They are bombarded by ideas spanning everything from putting kombucha in the fridge to launching a new product in a different industry.
Part of being strategic is recognizing that most companies do too many things, and most things don’t matter.
So the best strategic thinkers constantly ask themselves, “Who cares?” Who cares if 10 percent more people visit your website? Who cares if you can sell a product for $10 instead of $5? The numbers backing your idea have to connect to the high-level numbers in a meaningful way, or it’s probably not worth doing.
Most people stop turning the screw too early, pitching the opportunity but not the cost, or neglecting to calculate the full impact of the idea on the business. Keep challenging yourself with “so what?” until you can say “that’s what” in one simple sentence — until you can decide it doesn’t matter or can explain how it really does.
And it’s even worse when there’s someone else who knows the numbers better than you. You’ll know this is the case when you work on a project for a while, present it and then someone comes in and shreds your idea just by citing a few numbers.
Solving the problem involves figuring out why you didn’t have those numbers. Are the numbers easily available in a dashboard that you didn’t know about? Do you have to go talk to an analyst? Do you have to learn how to query a database and pull the numbers yourself?
To take control of the room, you have to establish that you know something valuable that no one else does. You have to know the numbers for your domain, and you have to know them cold.
But that doesn’t mean you need to memorize the numbers. Our director of finance, Chris Roske, has become famous for hauling around a one-inch stack of printouts packed with numbers and then lowering his glasses to flip through it when he needs data. It’s also fine to just use notes.
Don’t prioritize a fast answer over the right answer. When you’re on the spot, a delay of a few seconds can seem like an eternity, but if you need the time to get it right, you should take it. Citing a number is a way to make a small, definitive point, which gives you the standing and confidence to make larger, more speculative arguments later.
Starting from scratch: ‘We’ve already tried that’
Our culture celebrates breakthroughs. But many breakthroughs come about after a series of incremental steps and failed experiments. When you don’t know the history of what’s already been done, you risk running into a brick wall, with everyone telling you, “We already tried that and it didn’t work.”
One project I worked on was a dashboard for homeowners who are selling their homes with Redfin. Years ago, some engineers built a dashboard, and almost no one used it.
About every six months, someone would come up with a plan to update that dashboard. Sometimes people were completely unaware that an old dashboard existed. Others had ideas for improving the dashboard, but none for how to get more people to it.
We didn’t greenlight the project until a product manager put together a plan that dealt with these very legitimate concerns. And now, the Redfin Home Dashboard is one of our most popular features for homesellers.
So if you have an idea, assume someone else has already thought of it or is at least working toward it. Maybe it’s someone at your company, or maybe it’s someone in a related industry who faced a similar challenge.
Be relentless about researching what has already been tried and integrating those ideas into your own thinking.
The true spirit of innovation is figuring out how to overcome the challenge that blocked success before. It’s not developing an idea that has probably occurred to many others, but being the one person who sticks with it long enough to make it work.
Everyone will sit up and take note when you respond with, “Yeah, but we didn’t try it this way.”
Time: ‘What’s really going on in this business?’
Strategic thinking often happens over long periods of time as you watch how the numbers change, how competitors are behaving, how experiments are turning out.
But it can be hard to make time to, well, think. Especially if you have a job where a lot is expected of you.
Managers at Redfin often report that they don’t have time to be strategic, even though they want to be. It’s become almost a rite of passage for us to sit down with new (and experienced) managers to review their calendars and suggest ways to get time back for things like strategy.
But often the people who become strategic are the ones who are able to self-manage their calendars to make time for it. Scan your calendar each week; if you don’t have two hours at least for strategic thinking, you’ll keep running on the hamster wheel, never making progress on the strategy.
And then figure out how to get yourself into a mode where you can think creatively.
For some people, this means pacing in your office. For others, going on a long walk or run without a podcast and letting your mind wander over a tough strategic topic. Talking to someone else can help to clarify your thoughts, as you try to convince that person of your ideas. And writing down your thoughts in a few pages forces you to organize your thoughts and edit out the ones that are hard to explain.
Your goal is not just to solve the problems before you, but to figure out if the problems you are trying to solve are even worth solving. Go through your projects and ask yourself, “Should we even be in this business?”
Imagine that a new person is hired to replace you. What are the first three changes that person would make? Shake yourself out of the day-to-day grind, and try to see your business from a new perspective.
And then give it some time. If you want to be strategic, you’ll need to focus a great deal of your discretionary work time on being strategic, and it might be a while before you see the results. Many people simply give up too early on strategic thinking, going back to working on projects that are in their comfort zone.
Fly on the wall: ‘She didn’t really contribute’
People who want to be strategic often start out by trying to get invited to strategic meetings, believing it will benefit them to be a fly on the wall.
But then they go to the meeting and just listen, without contributing to the discussion. This sets them up as someone who’s not able to contribute strategically when, in fact, they were just trying to learn how these meetings work.
So it might be better to skip these meetings until you’ve had time to develop your strategic thinking. While you’re ramping up, ask to be looped in on the meeting notes, so you can follow along without attending in person. Then use the time to do the research and learn the numbers.
Before I joined Redfin’s executive team, I spent a year as a frequent invited guest to their meetings because I’d become the expert on certain topics, and the meeting couldn’t happen without me.
Your goal is to become indispensable on certain topics, so that people can’t imagine having that discussion without you in the room. And then you’ll never feel left out, because you won’t be.
Form opinions: ‘What’s your point?’
Before proposing a strategy, you will likely need to do research and then summarize it in written form. And then you find you have a fifteen-page document filled with statements like, “We could do this. Or we could do that. Or maybe this other thing.”
The document will probably also contain paragraphs that read like an eighth-grade algebra problem, outlining why this many contacts at this conversion rate result in this much revenue, or trying to explain the size of the market.
This is not a strategic document, but there could be a strategic document buried within it.
Go back through and cut all the mediocre ideas, so that someone else doesn’t have to do it for you. Go through the places where you are showing your math homework, and turn it into a simple chart or just a sentence with your main point. Take complicated ideas that would involve six different teams, and see if you can simplify it down to something that is easier to greenlight.
Then ask yourself, what would I actually do here? Does the reader know what I think we should do? Did I bury my best ideas in the middle of paragraph eleven?
State your opinions clearly at the very top, and then use the rest of the document to expand on your best ideas and explain your numbers. The ultimate strategic document paints the vision, but also includes an incremental step that your company can say yes to.
In the end, your document should be just like a treatise that slowly builds from high-level numbers to an exciting conclusion — only backwards and played at high speed, like when you reversed your Led Zeppelin album and heard the words of the devil.
State your opinions clearly at the very top, and then use the rest of the document to expand on your best ideas and explain your numbers. It’s okay to include questions, but if there are too many open questions, your job is not done.
And what if you aren’t a good business writer? It’s time to become one. You won’t be able to take on a large strategic scope that involves convincing lots of people unless you can put your thoughts in writing, because verbal pitching simply doesn’t scale.
The trend in business is away from flashy PowerPoints and towards clear business writing that reads more like furniture-assembly instructions. If you are better at verbal strategy than written strategy, try reading what you’ve written out loud and then improving upon it.
It can also help to read examples of good business writing. My favorite magazine is The Economist, which does a beautiful job explaining business strategy and numbers in a highly readable format.
Move on: ‘Got any other ideas?’
Great strategic thinkers have a portfolio of ideas that they develop over time. New strategic thinkers can often juggle only one or two. Of course, many strategic ideas get put on a shelf or killed altogether. But when it’s your first or second strategic proposal and it gets shelved, it’s demoralizing.
Getting through this is all about recognizing that some of the best strategic work involves figuring out what you shouldn’t do. If you can definitively settle a strategic debate, count it as a success. Leave a clear document with the reasoning so you or someone else can pick it up later, and then move on to your next idea.
Don’t get discouraged: ‘Has he hit his ceiling?’
You might be several years into your career before you truly get a chance to think strategically.
Maybe your company has a less transparent culture, one where you only get to see data about your project, and you can’t put the pieces together at a higher level until you get promoted a few times. But other people grow up talking about business strategy with their parents at the dinner table.
Your best bet is to treat strategic thinking just like any other career development opportunity, but one that might take longer than you are used to.
Find a strategic thinker whom you respect, and then watch what she does. When you get a chance to be strategic, ask for feedback so you can learn.
It’s harder to measure how good you are at strategic thinking than things like shipping a piece of software or hiring a team. But it can be learned.
Bridget Frey is Redfin’s chief technical officer.