Being Strategic - Think strategically in everyday work
Strategy isn’t just major company pivots. Some of the biggest strategic opportunities can be found in work you're already doing in the day-to-day moments.
“You need to be more strategic”
It’s feedback a lot of people receive as they try to move from middle management to the executive level. Yet, few can define what it actually means or entails.
Is it an innate talent, or some magic “X”-factor?
No. Being strategic can be taught and learned. It requires learning new ways of approaching problems, changing your mindset, and a bit of unlearning of the things that got us to where we are now. It requires picking up a few hard-skills and learning some very hard soft-skills.
Whether it’s analyzing problems, speaking the language of the business, or improving your bearing - the skills of being strategic can be taught.
This article is part of my series Being Strategic, a series of articles perfect for senior managers and directors who are attempting to move beyond operations and into executive-level strategy.
Strategy in the everyday
As a director or manager, you may be waiting to be pulled into a ‘strategic conversation’.
That’s unlikely to happen. A senior leader isn’t thinking “I’m going to pull this manager in to help them become strategic.” They’re thinking “This person thinks strategically so I’m going to pull them in to help me think through this”.
You have to be pro-active about being strategic before you’re trusted to be strategic.
Don’t lose hope though - any situation can be analyzed for its strategic implications. Strategy isn’t just major company pivots. Strategy is also in day-to-day moments and as a manager or director, there’s an advantage because there are so many day-to-day moments where the skill can be exercised.
Here’s a few real examples I’ve been through to illustrate.
The meeting derailment
During a meeting, a Senior Product Manager gets asked a question by the data scientist - “did you validate that this isn’t a seasonal quirk?” Perfectly reasonable. She started rambling, talking over the data scientist with hints of aggression.
The lens
The tactical lens - stabilize the moment:
Meeting facilitation - How do you get the meeting back on track?
Cultural modeling - How do you ensure that observers of that meeting don’t view that as acceptable behavior?
Corrective guidance - How do you ensure that the PM avoids a defensive reaction in the future for being asked a reasonable question?
The operational lens - diagnose if and why the system failed:
Standards enforcement - why did the product manager ramble? Was it simply a communication issue, or did they actually not know? If not - why did a Senior Product Manager not know their own data? Is this a training opportunity?
Consistency check - What other decisions are we making where we aren’t factoring in seasonality in our data assessments?
Collaboration opportunity - Why did this happen during the meeting? Couldn’t it have happened before it was presented?
The strategic lens - evaluate the tradeoffs and determine if they are worth it:
Decision tradeoffs - Are we making the right speed vs. rigor tradeoffs? Do we actually need or want data for this? For other things? Where’s the line, and what’s the impact of putting that line where it is?
Center of authority - If data materially drives a decision, who should own decision-rights? The person closest to the data, or the person responsible for the product outcome? If data isn’t important, shouldn’t data be more of an advisory role? Who should own this decision and what tradeoffs are we stack ranking?
Organizational capability - Do we want to drive more rigorous decision-making in this area as a de-facto standard, or is speed more important? What are our competitors doing? Is this a place where data moves the needle or does speed win out? Does it help us win, or does this just help us feel better about our losses?
What did I do?
I stepped into the conversation to redirect the meeting. “We’ll circle back to the data. Let’s stick to the agenda for now.” That kept the meeting on track.
I didn’t chew out the product manager in the meeting for not knowing their numbers - that would’ve led to more defensiveness, not less. I did talk with the product manager afterwards, specifically noting how that reaction wasn’t conducive to achieving the outcome of the meeting.
I also asked the Data Scientist how they felt afterwards to ensure they knew their contribution was appreciated.It led to a whole conversation about their perception of a lack of rigor they’ve been sitting uncomfortably with.
In my following 1:1s with product managers, I specifically requested deeper attention put into analysis and partnership with our data team before public presentations on work. I increased spot checks on analysis work and actively commented gaps, redirecting to data.
You get what you inspect. Afterwards, the team as a whole started ensuring that seasonality was a factor in their analysis. There were still some misses, but the rigor increased across the board.
Cross-functional mis-fire
A director of engineering posts an article to the company chat that is easily construed as villainizing and condemning a peer function, after a painful year of growing pains for that function. The director found it funny and enlightening, the function it villainized - not so much.
The lens
The tactical lens - contain the immediate damage:
Protecting morale - How do you make sure the peer function still feels respected and appreciated for the progress they have made while at the same time not stifling legitimate critiques?
Escalation control - How do you prevent this from rapidly turning into a public pile-on on a struggling function?
Immediate repair - Does the director need to clarify, apologize, remove the post, or follow up directly with the affected function?
The operational lens - diagnose if and why the system failed:
Director judgment assessment - Why did the director not anticipate how the message would be received? Was this a one-off lapse in judgment, or a pattern in how they communicate?
Leadership standards - Do our directors understand that their words carry organizational weight, or does that require renewed guidance? Are our leaders clear on what belongs in public channels vs. private discussions?
Cross-functional health - Is this incident exposing existing tension between Engineering and the peer function? How wide-spread is it, and does this need a relationship reset or repair?
The strategic lens - re-evaluate the tradeoffs and standards:
Cultural interactions - Do we want functions to challenge each other publicly, privately, or through a more structured forum? What model creates the best outcomes given our culture? How sharp can an honest critique be before it becomes corrosive?
Leadership bench depth - Is this director demonstrating the judgment required for increasing, broader influence, or is this a signal that they’re not suited? What does that imply for succession planning, promotion strategies, and future structural plans? Is this a sign of an underlying strength, and can it be directed productively?
Functional expectations - Is the peer function actually improving at the rate it needs to, or does it require a reset? Are the expectations on the function from the top matching those of peers? What level of friction between functions is healthy?
What did I do?
I messaged the director privately, asking them to reflect on how a peer function would perceive one of the leaders of another function publicly posting an article condemning that function.
While the director made some justifications, in the end they removed the post. I noted this as a potential improvement opportunity for the director as there were several other sporadic instances in the past - correctable, but not allowable at their level.
I had some follow-up conversations with a couple of members of the peer function who saw the post, hearing them out and ensuring there was no lingering concerns.
In my managerial 1:1s with my management reports, I ensured to re-emphasize the importance of communication tact.
I also worked more closely with the peer function to address its gaps and shortcomings.
Given the tremendous damage a lack of tact can cause and how important cross-functional collaboration was at our company, I held managers accountable to higher communication standard. Trust is not free.
Dysfunction function
The product organization has not been able to turn customer insights into direction at a pace that the company requires. You’re the engineering leader and have been working on providing feedback, support but more and more the responsibilities are falling on you and other non-product people to keep the company running. The company needs its product organization to get back on track - they’ve been delayed and halted from improving the product for over a year now thanks to poor processes, analysis paralysis, and low hiring bar. Product continually asks for more time, but progress and change is stalled. You’ve been working closely with the new VP of Product, and she has some good ideas but seems to conflict with the CPO on how it should be implemented or communicated. In the mean time, the product organization is blaming engineering for low quality and delivery speed, and market conditions for recent hits. The Engineering organization’s morale is at an all-time low and your own outcomes have started to suffer. The company’s largest spend has delivered nothing in a year.
The lens
The tactical lens - stabilize execution and morale
Execution containment - What needs to happen immediately to keep critical company work moving without permanently informally absorbing Product’s responsibilities?
Narrative control - How do you prevent Engineering from becoming the convenient explanation for Product’s misses while avoiding a public cross-functional blame war?
Morale protection - How do you keep Engineering from disengaging when they believe they are being blamed for problems they did not create and asked to compensate for failures they do not own?
The operational lens - diagnose where the operating model is breaking
Ownership clarity - Which Product responsibilities are being absorbed by Engineering? Which of those need to be returned, reassigned, or explicitly redesigned, and can they without losing productivity?
Leadership alignment - Where are the VP of Product and CPO misaligned? Does anyone else in leadership see a problem? What is their timetable for solving it?
Systemic failures - Are the delays caused by poor process, weak talent, unclear authority, analysis paralysis, executive disagreement, or something else? Who is accountable for solving them, and what authority do they actually have?
The strategic lens - decide what the company can no longer afford to tolerate
Functional accountability - How long should the company continue absorbing Product dysfunction before resetting? What is the cost of waiting another quarter? If a reset is conducted, what does that look like structurally and who’s best suited to pick up the pieces? Does Engineering and Product have the right current responsibilities, and is there alignment in leadership?
Company operating model - Should Engineering continue compensating for Product’s gaps to protect near-term outcomes? Can you fix the Product gaps if they are being compensated, or does it require the plate to drop?
Strategic capacity - What company opportunities are being lost because Product cannot effectively develop and execute a coherent product strategy? Is the current Product organization actually capable of supporting the company, or has it become a constraint? What value is the Product organization delivering today, and what do they need to deliver by next year? Are they on track, and if not - what’s going to fix that?
What did I do?
I kept the trains running. I ensured that the execution still continued and didn’t get stopped because of role boundaries. I coached our team on the importance of adaptability and initiative, promoting gap filling if it existed while ensuring we were deferring to our product peers - we were a startup, and sometimes we had to flex to get things done. We could make it easier for product partners by doing more of the heavy lift and proposing recommendations - at least in the short-term. I framed it as a growth opportunity and the way the industry was headed - engineers weren’t purely going to remain ‘tech’.
I worked as closely as I could in partnership with the Product leadership, noting issues, proposing solutions, and facilitating the implementation of their operational ideas to the extent I could without jeopardizing hard role boundaries. There was definitely a recognition there was a problem, but there was disagreement amongst the product leaders on the solution. I kept track of metrics and delivery, sharing with the product leaders so they could make better informed decisions.
Eventually, the organization reached a point where the cost-benefit of waiting for improvement no longer made sense. The product leaders departed, and I ultimately stepped in to redirect efforts - but that’s a war story for another time.
Situations are not ‘strategic’ or ‘not strategic’ by default. Moments and decisions can become strategic when you use them to change or reinforce direction. Every situation can be examined for signals and opportunities to influence future capabilities, manage organizational risks, improve systemic decisions, raise standards, or adjust other tradeoffs.
If you’re waiting to be invited into a room to ‘decide strategy’, you’ll never stop waiting. Strategy is all around you - you just need to use the right lens.
Get invited into the room by already being strategic.
Gefroh is the SVP of Product and Engineering at a technology startup in the health insurance domain. He writes extensively about Leadership, Strategy, and AI on his blog.
Feel free to reach out and ask any questions!