What is strategy, anyway?
Let’s keep it simple. A strategy is a living document that helps a group of people make aligned decisions over a span on time. When a team knows its strategy, their decision-making process is baked into the work that the team chooses or doesn’t choose to do, and those who follow the strategy have the confidence to make those decisions.
Strategy should be a living document. If your strategy is useful, it evolves with the conditions in the real world. Good strategy iterates, and a sign of effective strategic execution is a strategy that has a built-in feedback loop where the team sets a point, discovers what’s in front of it, and adjusts.
And if the adjustment says strategy needs to change? Well, you change it. But even reading that, ask yourself how often you and your team have iterated on strategy. Has the procedure been either everything works as written or the strategy is ignored? Be honest.
Why is that?
The strategy that you tried to execute is often blocked by the actions you take. You may want to change direction, but you don’t know how. When this happens, you’re usually being hit with the five deadly sins of strategy - a strategy that is hidden, ambiguous, untrustworthy, selfish, or stale.
The 5 Deadly Sins of Strategy
The five deadly sins represent obstacles that leave a team or a leader stuck. Each sin is the result of a failure in making the strategy a living part of the organizational fabric, from lack of visibility to rigidity in adaptation.
Here are the sins defined:
The 5 Deadly Sins of Product Strategy
- Hiddenness: Unseen or inaccessible strategies, leading to misalignment and disjointed efforts.
- Ambiguity: Strategies lacking clear objectives or target audiences, resulting in unfocused initiatives.
- Untrustworthiness: Strategies that fail to secure team buy-in, leading to resistance and low morale.
- Selfishness: Strategies narrowly focused on specific group interests, undermining collaborative efforts.
- Staleness: Strategies that don’t evolve with new information, leading to decisions with bad data that teams will drop.
The good news is that the first step to absolving yourself of these sin is awareness. Usually, they’re sins of omission, meaning they don’t happen because you actually mean to do them. Instead, they represent a breakdown in process, often driven by forgetfulness. That forgetfulness leads to confusion, product stagnation, and missed opportunities.
Overcoming these sins requires a deliberate shift in team behaviors and processes to ensure alignment. The team has to engage with the strategy, and by following the tactics here, you’ll have a much better chance at making your strategy match reality.
We will take a look at each sin from the eyes of different product teams at BobCo, a fintech company, including both how to identify and how to absolve your team from them.
1. Hiddenness
Hiddenness occurs when strategies are invisible or inaccessible to those who need to execute them, leading to misalignment and disjointed efforts across the organization.
How Does the Sin Manifest?
This sin often appears as confusion among team members about the organization's direction, priorities, and how their work contributes to these overarching goals.
For example, at BobCo, Jane and her portfolio leadership team spent the last few weeks of the year building a strategy to contend with the rise of AI in the marketplace. The team felt great about it, as it detailed the work necessary to make data more ingestible for AI use. After nine months of work, however, Jane and the team noticed that teams were seldom proactive, more often just wondering what was next. It became clear that no one know what the strategy was — they were acting on directives and nothing else.
Why should you Avoid This?
Without a clear and accessible strategy, teams cannot align their efforts towards common objectives, resulting in wasted resources and missed opportunities. Often, the most interesting work comes from the team working directly on the platform, and if the strategy is hidden, they miss out on the ability to be creative.
How to Fix It
Leaders should ensure that strategies are transparent and easily accessible. This includes regular communication through meetings, documentation, and open forums where team members can ask questions and provide feedback. As a leader, take some time to prompt your team about the strategy and their thoughts and let them know they are expected to engage.
At BobCo, Jane added a strategy session in the weekly planning meetings to discuss what had happened so far and how that may change the strategy based on everyone’s point of view.
If you find yourself on a team where hiddenness is a sin, ask these questions of your leader during a one-on-one:
- “Can you clarify how our current projects align with the company’s strategic objectives?”
- “Where can I find the most updated version of our strategy?”
- “We’d like to adjust our backlog against the strategy. Where can I find the most up-to-date version?”
2. Ambiguity
Ambiguity arises when strategies lack clear objectives, target audiences, or measurable outcomes, leading to unfocused initiatives and efforts. There is no who, what, where, why or when, i.e., the five Ws.
How Does the Sin Manifest?
Teams may pursue projects with zeal but without a clear understanding of what success looks like or how their work impacts the broader strategy.
Back at BobCo, Larry and his portfolio leadership team are excited about how energetic their respective teams are. After the planning session and a clear kickoff meeting, the teams set themselves up for success and were building some great products. After doing a post-mortem on the year, however, it became clear that while they were proactive, none of the features built on each other. They couldn’t learn anything that would help them get to their company vision.
Why should you Avoid This?
Ambiguity prevents teams from effectively prioritizing their work to focus cohesively, leading to inefficiency and a lack of progress toward any visionary goals.
How to Fix It
Define the five Ws and put them in front of everyone whenever strategy is mentioned or a new project launches. Every time you communicate, tell a story on how the last release helps inform this one.
At BobCo, Larry put this information front and center on the first slide in his next presentation to his team. We’ve launched this initiative — this is who it’s for. His second slide followed up by saying, “Our last release taught us XYZ and gets us further or closer to our objective in this way.”
If you find yourself on a team where ambiguity is a sin, ask these questions of your leader during a one-on-one:
- “How do we measure success for this project against the five Ws?”
- “How does this initiative serve our target customer?”
- “I’d like to tell a story to our stakeholders. Here are the main characters and challenges that I see. Can you check to see if I am aligned with our strategy?”
3. Untrustworthiness
A strategy becomes untrustworthy when it fails to secure team buy-in, often due to a lack of belief in its feasibility or alignment with organizational values, leading to resistance and low morale.
How Does the Sin Manifest?
This sin is evident when teams are reluctant to fully commit to strategic initiatives, possibly due to past failures or a disconnect between stated goals and organizational actions.
At BobCo, Hannah thought that she and her team had a great strategy, and those on the team felt empowered to get things done. That said, she found other stakeholders indifferent at best and hostile at worst when she needed information for the team to do its job. Finally, about nine months in, someone from sales pulled her aside and told her, “Everything you all do is a secret — product is a black hole. We don’t know what works or what doesn’t, so sometimes other departments feel like you and your team don’t always tell the truth.”
Why Should You Avoid This?
Trust is the foundation of effective execution. Without belief in the strategy or data to help teams understand progress, any efforts will be half-hearted and the desired outcomes will likely remain out of reach.
How to Fix It
Leaders should build credibility by ensuring that strategies are realistic, align with organizational values, and by demonstrating commitment through honest reporting on wins and losses. Spend time talking about wins and losses and how they affect the company vision. No one likes a perfect team, so spend some time showing that you all skin your knees as well.
Hannah made her BobCo product post-mortems public for other departmental leaders. This allowed them to see what hasn’t worked and how you plan on mitigating the issue moving forward.
If you find yourself on a team where untrustworthiness is a sin, ask these questions of your leader during a one-on-one:
- “I’d like to build relationships with team X. Who do you suggest I connect with?”
- “How do we handle failure? what is our protocol regarding pivoting?”
- “I feel pretty distant from other teams, so I’d like to share more data. How would you recommend I do that?”
4. Selfishness
Selfishness in strategy occurs when the planning and execution are narrowly focused on the interests of a specific group within the organization, undermining collective effort and collaborative spirit.
How Does the Sin Manifest?
This problem becomes apparent when initiatives primarily benefit one department or group, leading to silos and a lack of cooperation across teams.
At BobCo, Scott felt great about the strategy. He was sure that everyone else also saw its value because the first few launches were successful. The R&D teams felt empowered. People regularly shared the product story at the all-hands meeting. Everything felt good ... until he and the other teams did a retrospective and realized they had been transactional with other teams. Afterwards, Scott asked another leader in the organization, who told him, “Your strategy seems to be only about your team. People like you, so they help, but honestly, that goodwill is wearing thin.”
Why Should You Avoid This?
For a strategy to be successful, it must consider the interests and contributions of all parts of the organization. A selfish strategy can lead to resentment and a lack of support from those who feel excluded.
How to Fix It
Leaders should foster a culture of inclusivity, ensuring that strategies are developed with input from a diverse range of stakeholders and that benefits are distributed equitably across the organization. Ask other teams about what powers them.
Scott ran a lean coffee session with other stakeholders to get everyone on the same page. A lean coffee session involves inviting other team members into a light workshopping session, starting with a short presentation (less than 10 minutes) about the current situation. Then, you’ll have them ask questions and make comments, vote on the most important, and discuss them collectively. This workshop session often reveals what other teams care about so that you can change your language to address them proactively.
If you find yourself on a team where selfishness is a sin, ask these questions of your leader during a one-on-one:
- “How does this strategy benefit the organization as a whole?”
- “Have we considered the impact of this strategy on all groups?”
- “Is it possible for me to accompany team X for a day to learn how our product affects them?”
5. Staleness
Strategies become stale when they do not evolve in response to new data or changes in the external environment, leading to decisions based on outdated information that teams are likely to disregard.
How Does the Sin Manifest?
This sin is evident when teams continue to follow a course of action long after it has ceased to be relevant, ignoring new data or changes in the market.
At BobCo, Alicia and her leadership team spent more than three months crafting a strategy and found a lot of success over the first six months. That said, the second half of the year saw a huge drop in efficacy as feature usage dropped. At the end of the year, Alicia and her team did a retrospective, and when they made a timeline of events, they soon realized they never adjusted the strategy based on competitive data. As a result, their competitor picked up on the staleness and took market share as a result.
Why Should You Avoid This?
The business environment is dynamic. Sticking to a stale strategy can lead to missed opportunities and an inability to respond effectively to competitors or market shifts.
How to Fix It
Leaders should establish processes for regular strategy reviews, incorporating the latest data and feedback to ensure the strategy remains relevant and effective. Find a way to connect your long-term strategy with your quarterly goals and weekly planning.
For instance, Alicia added a section the team’s goal and planning sessions that asked, “What went wrong, and what should we change?”
If you find yourself on a team where staleness is a sin, ask these questions to your leader during a one-on-one:
- “How recently have we reviewed our strategic assumptions in light of new data?”
- “What changes in the market or our performance data should we consider in our sprint sessions?”
- “How can we bring new insights into our strategy?”
Absolve Yourself of These Sins
Overcoming the common pitfalls in strategic execution is crucial for any organization looking to succeed. By understanding and addressing the Five Deadly Sins of Strategy, businesses can improve how they create, share, and implement strategies. Leaders must lead by example, making strategies clear and accessible, and for every team member to engage with that strategy actively. This approach ensures that everyone is moving in the same direction, making the organization more aligned and efficient.
In short, tackling these strategic challenges head-on can transform the way an organization operates. By shifting from a static approach to a more dynamic and inclusive strategic execution, companies can better adapt to changes and seize new opportunities. This not only helps in achieving set goals but also promotes a culture of continuous learning and adaptation. Such a proactive stance is essential in today’s fast-paced business environment, enabling organizations to stay competitive and innovative.
