You just need to be more strategic.
I asked a handful of my friends and ex-colleagues: Have you ever received feedback that you need to “be more strategic”? Below are just a handful of the responses I received…
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I got a new leader and immediately lost all forward momentum in my career. Suddenly - I wasn’t strategic enough. Jokes on him though, we were laid off at the same time so he must not have been that strategic either.
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I have been given that feedback and ignored it, because anytime I would ask 'what does that mean?' I wouldn't get a straight answer.
We seem to throw the phrase "be strategic" around a lot, but no one can seem to agree on what that means in the startup world. When plans are changing so much and so fast there is no way I can plan ahead.
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I asked what it means and what I needed to be strategic and my (former) boss told me it's just something that people have - either you are a thinker or a doer, and it was an obstacle I needed to figure out on my own.
I asked again another time and got this: being “strategic” means you have an answer to “why are we doing this”? And, that answer includes something that matters to the leader of the org which usually boils down to either saving money or enabling the ability to make more money.
But it was obvious I wouldn't be able to do that in my role nor did I have the actual support from my leader and leaders to be "strategic."
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I have been told that, but my response was, “What does that mean? If you can give me examples or show me how I can do that I will.” They couldn’t back it up with any other answers or guidance. It was being thrown out as a way to justify not having any real answer for why a hire had failed or how we could do better with looking for a replacement. Be more strategic with sourcing and interviewing, but don’t change the profile we’re looking for.
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After asking a ton of follow up questions, “be more strategic” for me meant:
- Delegation and understanding how to scale myself
- Keeping myself in the advisor position, so saying “yes and..” instead of just “yes” but also saying “no” so I don’t slip into an order taker persona
- Evolving KPI’s from look backs to predictive insights
- Having an ongoing conversation of People v. Technology investments and trade offs
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Telling someone they need to “be more strategic” is code often used to create an arbitrary ceiling, mask some other feedback that can’t be spoken out loud, separate the managers from leaders - or individuals from that next step (getting that Senior or Lead title, or making the jump into management). It’s generic, abstract, slippery, and frustrating to receive.
So - in case no one has ever broken down what being strategic looks like, let’s do this together. Think of each of these skills as a layer or cumulative, one building upon the other. I tried to organize this from the bottom up with more foundational stuff first building up to more abstract ideas like understanding the big picture.
I’d love to hear your thoughts and feedback on if this is helpful in decoding this feedback or delivering it better - you can leave a comment here.
From Econ to English: go from math to data, data to information, and information to a story.
Being strategic means you know your math.
You know the inputs and outputs of your role - you can define the metrics (measuring your performance) and KPIs (how you’re measuring against a specific goal) associated with your work. You can also forecast based on this math what your capacity looks like, or create predictions and scenarios for the future. This applies to any role across any industry and is something you should start learning today regardless of your ambitions.
The AI prompt below should get you a relevant shortlist of metrics with the option to get more specific and then get benchmarks from similar sized companies or roles within your industry. From there, you can research how to measure each one and then look at the data and tools you have available internally to pull it all together.
Sample chatbot prompt: I'm working on learning the industry standard metrics for my profession. My job is [title] working on [2-3 main role objectives] for a [industry] company. What are the metrics specific to my role I should know?
Benchmarking is the comparison of how well other companies or individuals in comparable fields are performing. You’d leverage a benchmark to provide broader context for your performance using it as a goal, ideal state, or an acceptable range of performance. It’s important to understand what unique headwinds or tailwinds you may be facing regarding a specific metric vs an industry benchmark and build that into how you communicate performance.
Related - you can show your work.
It’s not enough to know how to measure your performance qualitatively and quantitatively (experience and data), but you need to know how to present it. A collection of metrics is a dashboard - but a briefing, presentation, a business case…that’s a story with your metrics underpinning the key plot points.
Dashboards - aka executive catnip. Not all dashboards are created equal. Resist the impulse to include every single metric. Group metrics into a theme that answers one key concern or question for the audience. (need help? find your nearest Chief of Staff)
Briefing (not a memo) - briefings are brief, they are summarizing a larger set of metrics, data, reports, or findings. Use these to quickly update someone on a situation and maybe influence a decision or provide a recommendation. (think: email or executive summary)
Presentations - monthly or quarterly check points on overall performance. Here you can show off longer trends based on bigger sets of data, get visual, expand on a narrative or theme. (quarterly business review, OKR updates, etc.)
Business Case - you have a problem (typically requiring money or people to fix it) so you’re going to outline this problem using data and observations, including the impact to/on the business, your proposed solution(s), solution costs, KPIs for success, and recommended next steps. (get good at writing these, pitching them, and then try doing this off the cuff to get buy in on anything you need)
From there, you need to be able to articulate and sell a vision.
This is beyond having a solid handle on performance and articulating that to others. Selling your vision typically revolves around change management (you’re doing something different in the how or the what of your job). So you’ll need to give people a compelling “why” in a way that brings them along for the ride and makes them advocates vs detractors for what you want to accomplish. This is the next step once the business case is approved, or a briefing leads to a new direction or decision.
Whenever there’s a change happening - regardless if you’re the one who decided to make the change - you have an opportunity to practice this skill.
First, understand everything you can about the “why” then layer in some of your own KPIs or how the success of this change will be measured, and finally - start selling. How you customize your messaging for each audience is key, so start with the people you work with regularly to test out tailoring your delivery.
Diplomacy: delivering bad news, managing up, and navigating grey areas.
Say the hard thing.
Being able to set boundaries, provide critical feedback, deliver bad news, or owning a mistake in a way that doesn’t fracture relationships and create friction is huge. Knowing your audience and their potential reaction to the “hard thing” is a crucial communication skill (this is building on delivering tailored messaging).
Here’s 4 hard lessons:
Don’t let things build and escalate. When we need to share something difficult we ask for advice from others, rehash the situation over and over, and procrastinate while in the background, things are coming to a boiling point. Make sure you think through timing and how the situation may worsen if you delay delivering news.
Owning your mistakes is all in the framing. I like this format: here’s the mistake, here’s why it happened, here’s what I/we are going to do moving forward. Simple, step by step. If you frame this with theatrics, apologizing profusely throughout, trying to spin it as a win, etc. you’ll lose your audience’s trust and instruct them on how they should act when something goes wrong - which only amplifies bad behavior vs productive behavior.
Delivering critical feedback: keep it direct, keep it clear, and keep it moving. Have your notes and practice a couple of times to yourself, dig into it directly “I have some feedback to deliver to you,” give the feedback, don’t get bogged down in litigating the details but do clarify the themes or behaviors you’re addressing, ask for their perspective, then find common ground on what happens next. Don’t tell someone to “be more strategic” and then mic drop.
Setting a firm boundary: focus on the actions vs feelings. Telling someone “I don’t like the way you made me feel when you ____” invites a discussion on the validity of your feelings. Instead try “This type of interaction can’t happen again because ____” and use a reason that focuses on the business, your role, the shared objectives, and the work. Try reminding everyone what role they’re playing: I’m the [your job title] responsible for [your mission] and I’m working with you, the [their job title], and together we’re going to [shared goal].
Understand you can steer the conversation! Some options might be…do we need to change the topic, end the interaction, pick this back up later? Give your audience time to process and formulate a graceful exit or a response without relying on jokes to lighten the mood or suddenly ending the conversation. This avoids someone feeling it wasn’t “that serious” or cut off without time to respond. Offer availability to follow up if they need time to think.
Manage up!
Get to know your leader: how do they best process information, what are their style preferences, what worries them, how are they thinking about the business, and on and on. Understand where you can enable your manager to be better through how you communicate and work with them.
Use your built in 1/1 time for this as you can, and a longer monthly check in for big picture questions.
When your manager comes back from a meeting without you, note what follow up questions they had and see if you can provide details on those topics regularly or address a specific issue proactively.
Flow information to them about internal political happenings, patterns you’ve noticed, etc. while avoiding gossip. Focus on data points from across the organization (what you’re hearing, seeing, experiencing) that will help build context for the teams and leaders they work with or are relevant to their own initiatives.
Work through the grey areas.
When you’re handed an unclear task or direction - do you ask 20 questions on how to accomplish it, or do you learn to ask 1-3 of the most critical follow ups and whip up a first draft before spending significant time on it? (Start doing the second option.)
This layers on top of managing up - it’s managing yourself and using what you know about your leadership to intuit faster and faster what they’re looking for so you’ve got it in their inbox before they even ask. At first this is going to feel like trial and error, but figuring out how to ask less clarifying questions each time will get you closer to being Proactive (sister to Strategic).
Think about what follow up questions are too redundant or broad, identify repeatable patterns in requests to scale, and get into a routine for iteratively reviewing and checking in as you work.
Being able to interpret a vague task from a new person will get easier as you start learning the best ways to quickly narrow in on the result someone is looking for. Starting with your own manager is the priority. Then, you can leverage that with cross functional stakeholders or external clients, and so on.
Big picture stuff: know the larger context, and understand how your business is driving towards results within that context.
Understanding goal setting within your organization.
This is beyond your individual metrics and KPI’s - you need to understand how your company sets organization-wide goals and how your team nests within that structure. So if your company has a revenue goal of $100M for 2025 - what goals does your team or function have that helps you reach that target together?
Here’s a checklist:
Identify your company’s goal setting framework (is it SMART goals, OKRs, KPIs, or?)
Find where your company goals are posted, make sure you understand each one and how they’re measured
Talk to your manager about your team’s goals and how they fit into the company goals
Draft your own goals and do monthly or quarterly check-ins*
*Do this even if you haven’t been asked to set personal goals. Align them within your team’s goals and do check-ins with yourself - log your progress and accomplishments and re-use for self evaluations or your resume. And, it’s great practice for practical application of goal setting frameworks.
Do not get tunnel vision.
You have to keep your head on a swivel and understand what is happening within your team, function, company, market, industry, and so on. Understanding and being able to articulate the macro (big picture stuff) and how it influences the micro (your day to day or a future decision) will help you with selling the vision and articulating data in a way that ties into what’s happening outside of your corner of the business. In parallel, you need to stay up to date on your own job function and advancements happening there.
Spend 30 mins to an hour every day reading about the market or industry your company is in, the products/services your company offers, and daily events (local, national, global) in that sector (can be from internal wikis or external sources).
Attend online events! There are so many free webinars, product demos, and online resources that you can engage with to learn more about your role and what’s happening within your function more broadly.
Develop a professional online presence by re-posting company updates, sharing professional milestones, commenting on industry news, connecting and following people in your industry.
Networking - set a goal to reach out to one person you don’t know but want to learn from in your industry and build from there. Networking can be as easy as asking a specific question, looking for a product recommendation, asking for a mentor session, or just being curious.
Now, you can just…be more strategic!
I hope this helps anyone trying to interpret this feedback and those who are trying to find a better way to deliver it. I’d love to know if this resonated with you or I missed anything! You can comment on my LinkedIn post here, or reach out directly here.
