Inner struggles of the Strategist-Executioner

I keep meeting different people who inhabit the same body. She has a Marketing title, or a Director title, or "Head of" something, and she is, at any given moment, doing at least four jobs, that used to belong to four different full-time people.

She has to look at the problem, define it, present it in a way that doesn't bruise anyone’s ego, but it’s still truthful. She makes sure to get input from the person at the front desk, who actually knows what's happening, because they always know. She translates all of that into language a board will understand and care about so that it goes into the strategic plan.

And then, once the plan exists, she has to go and do it. Campaign planning. Vendor management. Events. Budgets. Grant applications. Graphics. Photography. Video. Copy. Proofreading. Analytics. Convert, convert, convert. Get more donors, more grant funding, better open rate, higher engagement, increase revenue. Growth is somehow solely her responsibility too. She is fast and energetic! But I’ve never seen a post that said: “Welcome to the team, meet our new Head of Whatever!”

One job description, two roles

Strategists step back and get a bird’s eye view. They are asked see the whole shape of a problem from different angles. To experience some discomfort so that a usable insight has time to form.

Execution does the opposite. It needs you to get close, get specific, get it out the door, by this day, fast. It doesn't care how sophisticated your thinking was if the email wasn’t sent, or the vendor contract wasn’t signed. It definitely doesn’t care if the plan and the budget don’t align.

So she ends up grabbing the first strategic idea that shows up, so she can run with it, meet the deadline, hit the right percentages, and add a checkmark on the task tracker.

In a lot of industries, these two roles got separated on purpose. Someone creates the strategy, someone else builds the thing, but back in the day, the strategist and the executioner sat together and defined together what was feasible, and how it was going to to get made. In the nonprofit and mission-driven world, and in most small and mid-sized organizations, that separation never existed, and oftentimes fell on the lap of the ED, who’s wearing all the hats.

When I worked in the fashion industry, I've had to imagine the whole mood and character behind a campaign brief, fit it with the casting, combine it with hair and makeup, and then still figure out the mechanism for how the bags were going to look like they were flying (which meant getting my hand sliced by fishing line). I've done the event marketing strategy, and then shot the event photos, uploaded and organized them in a shared drive, then segmented the mailing list. I've been the communications director where the campaign plan, and the newsletter that went out were both done my hands. I've curated exhibitions where I wrote and proofread the press release in the morning, and hung the artwork myself in the afternoon. The muscle for thinking and the muscle for doing were never allowed to specialize.

Is specialization still trending?

Don’t get me wrong, I do believe that for you to know how something is well done, you need to know how to physically do it. I always think of the example I learned in college: in order to design a shirt on paper, I had to learn how to sew a shirt, in an industrial sewing machine, with actual fabric and thread that had to be budgeted and sourced, and a pattern that could be graded. Thats not specialization per se, that is design thinking.

Now the “Head of Whatever” is wondering if she could become just the strategist. Can she hand off the shoot, the vendor calls, the newsletter build, and only think? Some part of her isn't even sure that's a thing to want anymore, or if it's a fantasy she picked up by someone else's title, or someones calendar she’s never actually seen.

For a while, senior marketing roles did drift away from execution. Build the strategy, manage the team, manage the agencies, review the work, stay on the upper layer. “Do your time in the weeds and earn your way to the bird's eye view.” That was the promised trajectory.

I think that pendulum is swinging back. AI is raising the bar for what one person is expected to produce. Senior people are expected to be closer to the keyboard again, whether or not that was the plan. Which would be fine, except the calendar is already full. They still have to understand the business, the customer, the proposition, set the direction, present and persuade, lead people, analyze the numbers, and make the calls. Nobody handed them extra hours to go with the extra work.

If the tide is shifting back toward execution, does that feel like growth, since she's already spent years being both, already has the muscles nobody else on the team ever had to build? Or is she about to become an obsolete workhorse, a set of human hands outpaced by a tool, that learned to do the mechanical part of her job faster than she could ever teach someone else to do it?

I don't know if it has to be obsolescence, but it will probably only read as growth if she gets to choose where her hours go instead of just taking on more of everything because AI can do it.

The opportunity she is presented with isn't learning how to do more with the technology, and it's definitely not as simple as getting better at delegating. The real opportunity is building the systems that let you execute more, without spending more of yourself to do it. Learn what is worth tracking. Automate the reporting. Automate the data pulls. Build the repeatable workflow so you never have to build it from scratch again. Let anything mechanical be done by the machine, so the hours you get back go toward the thinking and knowing your team's (and your own) capacity, knowing your community and what they care about, which cannot be automated.

Automation makes a bad process faster too

We need caution. A lot of people are trying to automate a process before they've actually understood the problem. You can automate a donor journey without ever asking whether you understand the human decision to donate to your organization. You can automate a workflow, and simply make its friction points grind deeper. Automation amplifies whatever you throw at it. If what you hand it is a broken assumption about what your community actually needs, you now have a broken assumption running at three times the speed.

I would really love to see the time these tools free up to go back into understanding, not just into output. Otherwise we're not becoming smarter and better humans, we're just getting quicker at not being smart. And marketing isn’t just about promotion of a business, a product, or service. Marketing is about understanding human beings.

Who needs a seat at the table?

Effective marketing involves understanding how people think, feel and make decisions, which is psychology. There's a version of this work where marketing is treated like a vending machine: put in a request, get out a deliverable. Content production, lead generation, "make it look nice." Brought in after the decision was made and approved, and told what to deliver.

But marketing, done at the human level, which is what I'm describing, understands the customer, the community, the proposition, and the commercial or mission-driven goal, all at once, and how those things touch each other. It is not “support staff” work, but a seat at the table where the strategy gets shaped.

Meanwhile, be a human being

There is one part that doesn't make it into the strategic plan, and I’m gonna name it clearly. While you're holding the campaign timeline, the board's ego, the grant deadline, and the content calendar, you're also managing a staff of actual people, who have actual lives that don't match the fiscal quarter.

Meanwhile, you have to be sensitive to the fact that your front-of-house person's kid has an infection, and she is stressed because she needs to leave for a doctor's appointment, and then again to make sure the antibiotics get taken on schedule, because half-finished antibiotics are a terrible parenting decision.

Meanwhile, someone on your team is going through something at home they haven't told you about, and it's showing up, as a missed deadline, or as a poorly written message, and you have to decide whether to call them out or hold space for them.

What the Gantt scale doesn’t show

Knowing when to maintain the deadline, and when to let it stretch (without resentment, of course), is its own kind of expertise. It doesn't sound strategic, so this doesn’t go in the leadership job description or in the strategic plan. Acting out of compassion, and choosing to make space for somebody's parent declining, or a marriage that’s collapsing, or somebody who just needs to not come to work today but they can't say why, is also the job. It’s a leadership muscle, like the strategy muscle and the execution muscle, and it gets exhausted just as fast, maybe even faster, because it's invisible.

Nobody applauds you for it, it doesn’t get mentioned in the board meeting, but you take it on so a team member doesn't have to choose between their sick kid and their job.

I stand by this fact: an organization that “grows” on the back of people who are burning out to hold it together isn't actually growing. It is exploiting people's health, their families, their patience, their capacity. Sustainable growth has to make room for the fact that the people building it are also, at the exact same time, taking care of somebody's fever, somebody's grief, somebody's very human experience. Compassion needs to be part of the infrastructure, and not a soft female skill to deploy when and if there's time. Without compassion the whole structure gets compromised, and if your internal system is brittle, it will show up on the outside, no matter how good the strategy deck or the branding guidelines look.

Where are we heading?

I don't have a crystal ball, but I've been in enough rooms to make a few informed guesses.

I think the next few years split people into two camps: the ones who let AI absorb the mechanical aspects of their job, and reinvest their time into discernment, relationships, and understanding their community; and the ones who use AI to just produce more, faster, without questioning the deliverables. The first camp gets more valuable, and the second may get automated out from under themselves.

I think specialization can make a come back, but not the old kind of way. It won't be "strategist over here, executioner over there" again. It'll be more like: everyone becomes a strategist by default, because the execution layer gets cheap and fast, and the actual scarce skill becomes knowing what's worth executing. I’ve lived through this in the early 2000s when photography went from film to digital. The deliverables grew while the day-rates dropped, and the industry became about who could do what better and faster. The people who make it through this shift won't be the best at doing the most. They'll be the quickest at deciding how to do things and what shouldn't be done.

I think boards and funders will start asking different questions, too. Right now, growth gets measured in donors, dollars, return on ad spend. I think within a few years, some of them will start asking about retention of staff, not just retention of donors, because they'll have watched enough burned-out staff walk out the door, and they will notice the pattern. Compassion as infrastructure hopefully will stop being a nice idea, like DEI, and starts being a line item, because the alternative is costing them their best people.

And I think the seat at the table gets harder to win, not easier, even as marketing gets more central to the mission. More people will claim they can do it, because the tools make the output look easy. Fewer people will actually understand the human being on the other end of it, because they never learned how to make the shirt to begin with. That gap is where the opportunity sits.

None of this is a promise. It's a bet, made by someone who's already worn every hat in store, and is trying to figure out which ones are actually worth keeping on.

Protecting space

Most of us reading this aren't choosing between strategist and executioner. We're both. And most of the time, that’s fine, as long as we are ok with going broad. Another skill we have to learn is how to protect the space.

Can you protect enough space for thinking and being, or are you getting pulled back into the doing?

Seems to me that the people who will feel accomplished in the future won't get there by avoiding execution. They will execute fast, use tools wisely, manage compassionately, and protect the space where the good ideas get to arrive.