Why “Be More Strategic” Is Bad Advice

The Introverted Executive Podcast: Why “Be More Strategic” Is Bad Advice

Have you ever had somebody tell you that you need to be more strategic?

Maybe it happened during a performance review. Or maybe you applied for a more senior position, somebody else was selected, and when you asked for feedback, you got some version of:

“You did great. You just need to be a little more strategic.”

Okay.

What exactly are you supposed to do with that?

I was given that feedback once, after interviewing for a senior position.

I had not been selected, which was fine. I knew the person who was selected. That person had a lot of knowledge and experience that was different from mine, and I had knowledge that was different from theirs. I think either of us could have done the job well in different ways, and either of us would have had things we needed to learn. It was mainly up to the hiring panel about which of us would address their most pressing concerns.

But after the selection was finished, one of the people involved told me that I had made the competition difficult, and that I was the alternate if the first candidate did not accept. I asked whether there was anything I could have communicated during the process that would make me a stronger candidate next time. His advice was that I, “Needed to be more strategic.”

And, I remember being annoyed by that.

Because during the interview I had mentioned some extremely high-level north stars. I was talking about alignment to the National Security Strategy, the National defense strategy, and the CNO’s strategic plan. I talked about senior Navy and Pentagon-level requirements. I discussed what our fleet customers needed and how those requirements were formally initiated and validated. I talked about integration across programs, other program offices, and broader capability solutions.

So my immediate thought was basically: How much more strategic would you like me to be?

But after I got over being annoyed (HEY—I am human, okay?!) I kept thinking about it.

And over time, I realized there actually was something useful for me to learn.

It just didn’t come through in the overly simple sentence, “Be more strategic.”

That is the problem with this kind of feedback.

It sounds like important executive-level feedback, and it may even point toward something completely legitimate.

But unless somebody can explain what they actually observed and what they expected to see instead, it is not very useful developmental advice for someone who wants to improve her actual strategic understanding.

And I really do not want you to go home after somebody says that to you and decide it means you just don't get it.

If somebody tells you that you need to be more strategic, it would be very easy to decide:

Maybe “I'm just not strategic,” or “people at that next level understand something I don't get,” or “I guess I am really good at execution, but I don't have whatever it is executives have.”

I do not want you making that leap.

Also, it doesn’t mean the feedback you received is wrong.

It may mean that you have something important to develop in the way you connect strategic intent to day-to-day execution. Or the issue may be how clearly you communicate what you are really thinking about—from what leadership cares about in this organization to where the overall industry is heading.

But the phrase “be more strategic” does not tell you what that thing is.

And before you turn somebody else's vague impression into a conclusion about your overall capability, I want you to get curious about what they actually mean.

Because there are a lot of very different things that could be wrapped up in that sentence.

Maybe you are thinking too narrowly about your own part of the organization.

Maybe you understand the larger strategy, but you have not connected it clearly enough to what your organization actually needs to do.

Maybe you see the whole problem but you’re not making a clear recommendation.

Maybe you are making good strategic decisions and nobody evaluating you understands the thinking behind them.

Those are distinct gaps, and each one requires a different focus.

There absolutely are people who are excellent at their jobs and also need to become more strategic.

One of the ways I see this happen is when somebody becomes very focused on their own piece of the organization.

She knows her program, project, technical area, and exactly what her team needs. And she may be completely right about what would make her particular piece of the puzzle better.

But her project or department is not the whole organization.

Imagine you are leading a cross-functional team and you bring a recommendation to a senior leader.

You coordinated with everybody you thought you needed to coordinate with.

You did the analysis and are convinced that your recommendation is right.

And then your boss says something much more useful than “be more strategic.”

Maybe she says:

You did a good job understanding the problem from your department's perspective, but I expected you to talk to our CFO, CTO, and Operations leaders too. This decision changes our financial strategy and our technical strategy, and I do not see either of those perspectives reflected in your recommendation.

Now you have something to work with.

Maybe you really were seeing the problem too narrowly. That does not mean you are incapable of strategic thinking.

It means your field of view needs to get wider.

Because at some point, especially as you move into senior leadership, your job is no longer simply to advocate for your own part of the organization.

You have to understand that other people may have perfectly legitimate reasons for wanting something different from what you want.

Finance may have a constraint you do not see.

Technology may have a dependency you did not know about.

Operations may know that something that looks easy on a slide will be nearly impossible to execute.

The customer may care about something completely different from what your internal team thinks is most important.

The supply chain may be changing.

A new regulation may be imminent.

The industry itself may be moving in a direction that changes the risk calculus.

You do not have to personally become the expert in every one of those things.

But, you do need to become curious about how the larger system works and try to see evolving risks and opportunities.

Because you can be completely right about what is best for your function and still be wrong about what is best for the organization.

This was one of the things I eventually realized about my own interview.

I had gone very high level: national strategies, Department of War strategy, Navy strategy, Pentagon-level requirements, and senior-level alignment. All of that is important.

But there is a difference between knowing the high-level strategy and showing how you would execute it inside the organization you are actually being asked to lead.

Once I had this breakthrough, I felt like my brain made a million connections at once.

Because if I am interviewing to lead an organization several levels below the Pentagon, there are a lot of things that happen between the national defense strategy and what my organization actually does on Monday morning.

How does that strategy become our priorities?

How does it affect our budget?

What capabilities do we need to build?

What work should stop?

What needs to be integrated with another program?

What risks do we need to accept?

What decisions belong to us?

What decisions need to be elevated?

What does this mean for the customer?

It is absolutely essential to map the connections from the larger strategy and vision to your own organization and the way your industry is evolving, then give your departments milestones or benchmarks that support that direction.

And I think this is one reason people sometimes sound very strategic without actually demonstrating strategic judgment.

They know the big words and the company vision. They can quote the strategy and mention the CEO's priorities. But can they tell you what those things require from the organization they actually lead?

That is different.

For me, strategic executive judgment starts with understanding where the organization is going.

If you are the CEO, you may be the person shaping a significant part of that vision.

If you are somewhere else in the organization, you need to understand the vision and why it matters.

Then, within your scope of responsibility, you make decisions that help move the organization toward that future.

And this is important: you are not making the decision based only on where the organization is today.

You also are not making it based on where you personally wish the organization was headed.

You have to deal with reality.

What resources actually exist or are likely to exist?

What risks are we accepting?

What constraints do we have?

What do our people know how to do now or what can we do to uplevel their knowledge?

What technology is available?

What commitments have already been made?

What does the customer need or want?

What is changing around us – in any of these areas?

When you understand as much of all of this as the decision requires.

Then you can ask:

Given where we are, and where we have said we are going, what is the best decision I can make within my authority?

And if the decision is not yours to make, then part of your responsibility is to elevate it to the person who does have that authority with enough information that THEY can make a good decision.

To me, this is much more useful “strategic behavior” than somebody simply telling you to “think bigger, think strategically”

There is another possibility I want you to consider:

You may already be doing more strategic thinking than other people realize. This connects directly to something we talked about in the “Dependability Trap” episode. Sometimes the invisible part of your work is not how hard you worked. Sometimes it is how well you thought.

You may recommend “Option B” because you have already considered the customer, the technical risk, the budget implications, what another department is doing, and what the organization is trying to accomplish in the next year. But, if you communicate only the final answer, everybody else hears, “Tina recommended option B.” They cannot see what you noticed, what you connected, assumptions you made, tradeoffs you considered, or the risk you are trying to mitigate.

If none of that reasoning is visible, the person evaluating your readiness may genuinely not understand how you arrived at the decision. That is not the same as not being strategic, but it can create the same career result.

One example of thinking strategically but not communicating strategically can be seen during interview panels that I have sat on over the last 10 years:

There have been multiple times when I have been on interview panels, interviewing people for very senior positions, and occasionally someone will do the opposite of what I did in the interview panel I mentioned at the beginning where I went TOO big picture without connecting it back to the execution at the organizational level.

Let's say we schedule a 45-minute interview and give the candidate five or six questions.

Every now and then, someone will literally answer only the exact question put in front of them – as if they are interviewing for a mid-level manager position. I KNOW they have a strategic understanding because maybe I have worked with them before, or I know them by reputation and accomplishments.

Then, at the end, we will ask, “Is there anything else you would like to add or expand upon?” This is an example of the panel “Knowing” they are capable of a more robut response, and we are trying to coax it out of them… yet, they will say “no,” they have nothing else to add.

The entire interview may end after 15 minutes.

For a very senior position.

The problem is not that we wanted them to ramble for 45 minutes. We definitely did not.

What we were trying to understand was whether they understood the scope of the responsibility they were asking to take on and the level at which they would be expected to lead.

We did not want them to answer the question only as an action officer who had been given a single task to accomplish.

We wanted to hear how they would think about that question if they were responsible for leading the organization.

What vision would they have?

How would they move people toward that vision?

How would they strategically plan and execute whatever issue we had put in front of them?

At some point, especially as you move into more senior positions, answering the literal question is not always enough.

You need to understand why they may be asking it.

How does that question connect to the scope and seniority of the position?

If you were actually in that role, how would your answer affect the organization?

What would your priorities be?

How would you approach the responsibility?

And I have interviewed people who seemed to walk into the room practically expecting that they would be selected, but they said so little that it was genuinely difficult for us to understand what they would actually do if we gave them the job.

Even when we tried to draw out more information, sometimes the answer was literally, “No. That completes my response.”

And then we had almost nothing else to evaluate.

So, when you are interviewing for a more senior role, I am not suggesting that you talk just to fill the time. There is an opposite problem where somebody says far too much and, after all of those words, you still do not know what they actually think.

You want to be coherent. You want to answer the question that was asked.

But you should also understand the scope of the position you are interviewing for and think:

Why are they asking me this question?

How does this question apply to the responsibility and seniority of this role?

And what do they need to understand from my answer about what I am capable of, how I think, and how I would approach this job?

That is very different from simply answering the question in front of you.

Eventually, when I interviewed for the position I am in today, I had developed a literal 100-day plan. I had already thought through what I would do in the first couple of weeks, what I needed to understand in the first month, what I would work toward by 90 and 100 days, and the direction I wanted the organization moving during the first year.

I am not telling you that everybody should walk into every interview with a 100-day plan. The important change was that I had stopped thinking only about how to answer the questions. I was thinking about the job, and I knew what I wanted the interviewers to understand about how I would approach the responsibility, if they gave it to me.

When a question gave me a legitimate opportunity to explain part of that thinking, I could. I still answered what they asked; I did not force a memorized response into the interview. But when the interview ended, they understood more than whether I could give a technically correct answer. They could see something about how I would actually lead.

I believe that made a difference, although I cannot prove that my 100-day plan was the reason I was selected. There are always multiple factors in a hiring decision. What I do know is that it changed the quality of the way I communicated my thinking, and that was valuable whether I got the job or not.

When I think back now to the person who told me I needed to be more strategic, I still do not know exactly what he meant.

Maybe he thought I was operating too high and had not shown enough connection to execution. Maybe the person selected had a stronger budget or contracting strategy, while I had a stronger capability or integration strategy, and maybe they needed that person’s superpowers more at that time. Or maybe he noticed something completely different. I do not know, and that is exactly why better feedback would have helped.

Imagine if he had said, “You understand the high-level strategy, but I needed to hear more about how you would translate that into the priorities and decisions of this specific organization.” I could have examined that. The same would be true if he had said that my technical and integration thinking was strong but he needed to hear more about my budget strategy, or that I had not explained enough of my reasoning for the panel to see it.

Any one of those responses would have given me something I could use. “Be more strategic” did not.

So, if someone tells you that you need to be more strategic, and the circumstances allow it, ask for examples. You can simply say, “Can you give me one or two examples of where you saw that gap, and what you would have expected to see instead?” That is a reasonable question from someone who is trying to learn.

If they give you a real example, pay attention. Maybe you are staying too close to your own silo, not connecting the higher-level strategy to execution, identifying issues without recommending decisions, or missing an area of the business you need to understand. Now you have something you can develop.

If they cannot give you an example, that’s information too. It does not automatically mean the feedback is wrong, and it does not prove that somebody is trying to hold you back. But I would not take an unexplained impression and turn it into a final judgment about myself.

One minor warning… Please do not hear this episode and start trying to sound strategic by using bigger words, mentioning the CEO's vision in every meeting, or refusing to pay attention to details because somebody told you that executives should stay out of the weeds.

Sometimes the detail is exactly where the risk is hiding, and sometimes you need to understand it before you can make a responsible strategic decision. The question is whether you can connect the detail to something larger: the technical issue to the customer, the customer to the strategy, the strategy to the budget and priorities, and today's decision to where the organization is headed.

That is the kind of thinking you can develop and the more responsibility you take on, the more important those connections become.

For your experiment this week, choose one piece of work that is already on your plate—a project, a recommendation, a decision, or a problem your team is trying to solve. Do not try to examine everything. Choose one thing.

Ask yourself, “What else does this effect in our organization or our overall industry?” Find the one connection that seems most important to understand.

Then ask, “What does that change about what I would recommend, prioritize, stop or start doing, or communicate differently?” Learn one thing you did not know and see whether it changes the way you think about the work you already do.

If somebody tells you that you need to be more strategic, I do not want you going home and deciding that you are missing some secret executive capability everybody else somehow understands. Maybe you have something to develop. Most of us do. I certainly did, and I continue to evolve.

But find out what the feedback actually means. Ask for examples when you can, examine your own work, and let the evidence show you whether you need to broaden your view, connect strategy to execution, make a clearer decision, or make more of your reasoning visible.

That still leaves another problem. You can become much better at seeing the larger system, develop stronger judgment, and create evidence that you are ready for more—and still be sitting in a job you never particularly wanted, waiting for somebody to give you the perfect developmental opportunity.

Sometimes they will. Sometimes they won’t. So in the next episode, I want to talk about what you can do with the opportunity you already have now, including a job you may not want at all, and how you can turn it into preparation for the job you actually do want.