How do you know what to do?
Before I was a meddling executive myself, I used to lose sleep over executive meddling. Why can’t they just trust I know what I’m doing? Why can’t they just let me do my job? Could they please stop going in and changing things, or changing good work, or changing priorities, or focusing on whatever the “new thing” is that’s caught their eye?
And then I became an executive and I realized that all that stuff was the result of uncertainty. If I, as the executive, don’t understand the plan to grow a marketing channel, how can I trust that there is a plan, and that it will work? There’s a reason that the more senior you get, the more you value hiring — it’s the people on your team that make most day-to-day decisions, and on a great team it’s also those people who tell you what they should be working on.
This is the biggest career leap most people don’t make — transitioning from “working on projects because your boss assigns them to you” to “proposing what the work should be (and what resources you need to execute).” I’ve talked around this idea before (in How (not) to present an idea, in Does your job title matter, and in Are you a task solver or a problem solver) but there’s always been something missing, and that something is the answer to the title question.
How do you know what to do?
Most people don’t come up with strategy of their own volition (if you do this, you already stand out in a pretty major way), and when they do it tends to take the form of “we should do this.” I’ve gotten a lot of “we should do this” proposals in my career, and most of them have one of these problems:
(Most common) It’s a list of “things to do,” not a clear thesis about the approach that will lead to success.
It’s a plan that’s too narrowly focused on a small piece of the business, usually the part of the business that the person proposing it specializes in
It’s a plan that would be cool but isn’t going to work in the context of this business because of some combination of resourcing and competing priorities
It’s a plan that doesn’t request any sort of additional resourcing or cross-team coordination, which makes it siloed (and probably too small in impact).
There are about 10 kajillion “strategy frameworks” that people use to put together their proposals, and I’m not going to give another one here. Instead, I want to drive home the idea that strategy doesn’t happen all at once — it emerges as you let information from the business flow through you.
First, a mistake. You don’t come up with strategy all at once.
I have heard some version of this phrase from multiple people I’ve worked with in every job — I feel the need to say that 1) to point out that it’s common and 2) because lots of people I’ve worked with read this newsletter, and I want to say “hey! This is general advice and it’s not addressed at you specifically.”
Mistake: “I need to sit down to think and really figure out the strategy.”
Reality: When you have the most important information from the business flowing through you, the right direction (or at least “a” right direction) appears almost out of thin air. When you sit down, you are usually documenting something that’s mostly already in your head — not coming up with it from scratch.
Also in every job, I’ve been that guy who makes stupidly long Google Docs about what we should do next (people I work with now won’t believe this, but I’ve reigned it in over time!). Usually they don’t take that long to make, and people comment on that a lot. I sit down, I start typing, and 90 minutes later I have 2500 words and a table of contents.
The key to this is that I’m not sequestering the work of strategy into the days where I have long interrupted blocks of time to think (also, you can add a table of contents by hitting “Insert” → “Table of Contents”). Frankly, I don’t have enough of that to have it be the only time I’m thinking about what we should do.
By the time an idea appears in a tolstoyesque Google Doc, I have been thinking about it for weeks, months, or even years. As an example, Podia recently added a new plan tier. I put together the case to change it ~3 months before the change — but the first mention of a similar plan at this price point appears in a deck from over two years ago.
Strategy isn’t something you can just come up with on the spot, and expecting yourself to do it in one long “think and figure it out session” is part of the problem. You have to be thinking about strategy all the time.
“You have to be thinking about strategy all the time.” But isn’t that hard?
Thinking about strategy all the time is hard if “thinking about strategy” means “set aside many, long, interrupted blocks of time to think through a specific problem.” But deciding what should be done rarely looks like this.
Here’s decision researcher Gary Klein, summarizing some findings in his book Sources of Power:
“Mosier (1991) studied videotapes of twenty-three three-person crews, consisting of qualified commercial airline crews, flying a full-mission simulation in a Boeing 727 simulator. She found that ‘most crews did not wait until they had a complete understanding of the situation to make and implement decisions. Rather, they seemed to make a recognitional, almost reflexive, based upon a few, critical items of information; and then spent additional time and effort verifying its correctness through continued situational investigation. If later information changed situation assessment enough to prompt a change of decision, a second option was generated and implemented. Virtually no time was spent in any comparisons of options. In fact, the bulk of time was spent in situation assessment than alternative generation for all crews (p. 269).’”
Strange! Experts don’t seem to spend much time on pro/con lists. They don’t tend to consider multiple courses of action at all — in fact, they spend most of their time understanding the situation.
This is what I mean by thinking about strategy all the time, and it’s what I meant above when I said “when you have the most important information from the business flowing through you.”
On any given day, you should have ready, regular access to:
Qualitative information about how the business is doing — stories from employees, comments from customers, support chats, online reviews, survey data, and other information.
Quantitative info about the business — revenue, new business, churn, whatever other metrics make sense for the context you’re in.
Background information about how your specific field works. This may be research-based information (e.g. all marketers should read How Brands Grow) or it could be case-study based (it is useful to have examples to draw on to prompt ideas).
Looking at numbers, comments, survey results etc. on a regular basis is not nearly as time or energy-consuming as a long sitdown (although it can take several long sitdowns to figure out how to make this information readily accessible), but it will prompt ongoing, regular, better-informed thinking about the state of the business and what should be done next.
When I started at my current job, the first thing I did was put together a customer research doc and talk to 15 customers — hour long, paid interviews where I dug into what their lives looked like, what their businesses looked like, and how they used our product. I’d have done two hour interviews if I’d thought it feasible.
Here’s Klein again, writing in a different book (Seeing What Others Don’t) about how his team changed Procter & Gamble’s approach to a product line with qualitative research.
“My three colleagues and I formed ourselves into two teams and interviewed a total of twelve homemakers for the two days. That was it. The P&G team was used to sampling hundreds of female heads of household with each survey. The P&G team couldn't believe we could get anywhere with twelve interviews. But their telephone surveys took about ten minutes. Our interviews lasted two hours. The P&G researchers had trouble believing that we could spend an entire two hours talking with one homemaker about a very simple decision.”
I took the hour-long interview transcripts and marked them up by hand, then used a qualitative coding approach (decent primer on qualitative coding) similar to Jobs to Be Done to get better insights out of the data.
Since that project we’ve done lots of work to increase the flow of information — recently my colleague Marc Thomas figured out how to use GPT + Zapier to consolidate insights from across surveys and categorize the responses automatically, and everyone on my team has become aware of my obsession with process behavior charts — but that’s the basic idea.
You can’t make good decisions in a situation unless you have a good understanding of that situation. But also the nature of business is that you can’t sit around waiting for perfect information before you do anything. So you have to figure out how to successively improve your understanding of your situation while acting at the same time.
So what’s the answer to the question of “how do you know what to do?”
First, you have to be thinking about it all the time. You are always, constantly, building and updating a model of how your business works in your head. That’s a model of your customers, your market, the internal team dynamics — everything. Just by trying to update your understanding of the business you are going to come up with more and better things that should be done.
Second, you need methods that bring you a better understanding of your situation. I’ve read thousands of support chats, reviews, interview transcripts, survey results, etc. etc. Knowing what you need is easier said than done, but getting some skills in both qual and quant research is pretty important. I think learning about semi-structured interviews and process behavior charts is a pretty awesome starting point.
Third, you need to understand the general underlying principles of your discipline. You can build business expertise through studying the fields underlying business, and by reading narrative-style business case studies (in fact, research supports using both methods, and I would do both). Simple analogy: if you’re learning to play guitar, learning more chords will open up new worlds of the music you can play.
Fourth, and finally, you need to get the information of your specific business flowing through you so that it mixes with the general principles of your field. If you’re successfully getting some kind of insight fed to you on a daily basis, you’re always thinking about your business and you’re always thinking about what you could do to improve it.
The plans that emerge from a long, uninterrupted planning session are usually bad. Unless they’ve been preceded by a longer period of continuously updating an understanding of the business. They tend towards lists of things to do, and they struggle to dig past surface-level ideas that will grow the business and get an executive off your back.
To bring it back to the meddling executive, here’s what legendary coach Bill Walsh did when he took over the terribly losing 49ers.
I felt I could turn things around, but I needed to buy time. I did it, in part, by keeping Eddie Jr. in the loop; fully informed—perhaps overly informed—on every single phase of the operation. This included providing him with a budget manual (thick), an operations manual (thick), a personnel manual (thick), an overall set of job descriptions that included the specific job of each player and my evaluation of that individual (thick), and a detailed listing of my performance goals and expectations (even thicker). On and on and on. Paper. Paper. Paper. The information was not frivolous "filler," but substantive and sizable. I wanted the owner (and his advisers) to understand that I was applying maximum effort and paying attention to every single solitary detail of the family's massive financial investment. I believe the voluminous detailing of my efforts and plans bought me previous time.
If you want to keep meddling executive out of your hair, you have to give them confidence that things are under control. The easiest way to do that is to remove uncertainty — and the best way to do that is to show them a plan that will clearly get them what they want.