Walking the tightrope between the pie in the sky and the deep weeds

By: Yariv Adan

There is a frustrating gap between the ability to imagine what product could orshould be built, and the actual pace at which things can be done. The gap mostly has to do with available resources, appetite for risk, operational constraints, and the complexity that unveils as the team progresses from an oversimplified idea to an actual product plan. Yet, a team that wants to build products that change the world, must learn to bridge this gap. On the one end, have a healthy disregard for the impossible, in particular when it comes to vision, setting goals and brainstorming ideas. And on the other, be laser focused on execution with meticulous attention to detail. The role of a product leader is to constantly manage that balance — challenge the team to think creatively and strategically when needed, and introduce discipline in planning and execution at other times.

But as straightforward as all of this may sound, reality has proven that doing it in practice is much less trivial, and many leaders fail in guiding their teams in this manner. One root cause of that has to do with the personal bias of the leader. Different leaders tend to naturally bias to one end of the visionary-operational scale, more than to the other end, and as a result create imbalance for the entire team. Moreover, often the leader is unaware of her own bias, but the team members pick it up, and as they try to please her, they amplify the outcome.

Over the years, I have learned that my own personal bias is more towards the strategy and out-of-the-box thinking — “You can dream what you can’t build, but you can’t build what you can’t dream” is my personal mantra. But I also learned that challenging what’s possible with creative ideas is not always inspiring for the team, and sometimes can even be annoying and disruptive. So I have been on the lookout for tools that neutralize that bias, and allow the team to strike a healthy balance between visionary brainstorming, and flawless execution. The framework detailed below does exactly that, and is straightforward to implement, as if following a playbook:

Setting an audacious mission and goals — Have an overarching mission that stretches what currently seems possible, yet is measurable, and reflects what success would look like. Don’t be concerned about sounding disconnected. While they might push back at first, eventually teams tend to grow to the challenges presented to them. We live in an era in which a small set of companies develop self driving cars, advanced robotics, and breakthroughs in AI. Don’t let your team set a low bar for themselves. Once you set the mission, make sure that all your leads are familiar with it and agree with its relevance — every member of the team should be able to recite the mission and say why they think it is important or meaningful for them. The mission can be 1–5 years out, that’s fine. Make sure you have audacious annual goals which tie to your mission. The art of leadership is all about having your team take these goals seriously and work as hard as they can to achieve them, but not to feel complete failure if these are not achieved. One way to proactively mitigate that, is to list in detail the prerequisites for success. Then, it’s easier to review which of the assumptions were false and why.

Make place for at least one annual wild brainstorming session — I find 2–3 day comprehensive sessions based on the Osborn brainstorming method to be very effective. Though make sure to get an experienced facilitator (there is endless information on the web, with IDEO being most famous for applying this method).

Schedule bi-quarterly, detailed strategy reviews — answering these questions:

  • Do your strategic assumptions still hold? What should be the new assumptions?
  • Are your mission and annual goals still relevant? How should they be modified?
  • Are you on a path to achieve your goals? What should you be doing differently?

Have quarterly goals and leads-reviews, bridging strategy and execution — Make the quarterly goals measurable, unambiguous, and with dates attached. Quarterly goals relate to tasks completed within the quarter, not necessarily at the end of it. In your reviews, spend a short time at the beginning reminding everyone of the strategic annual goals, and highlight any major change in the assumptions. Next, review how you did against last quarter’s goals. Spend the rest of the time reviewing the execution of your key projects. Focus on the cross-team / cross-functional aspects of your projects. Identifying missed dependencies, and resolving cross-team misalignments is usually more challenging than intra-team issues, and will often require the intervention of the lead to resolve. Have the next quarterly goals (or at least the detailed guidelines for these) as the outcome of these reviews.

Schedule bi-quarterly, detailed planning and execution reviews — Get into the details, and challenge the team where appropriate. Show, don’t tell that meticulous planning and execution are most critical to the success of the team, and are extremely important to you.

Foster a culture of planning and execution — demand from your leads to have weekly team meetings, reviewing and reporting status.

Hiring — Most people tend to appreciate and hire people who are similar to them. Especially when it comes to visionary vs operational bias. Do the opposite. Hire at least one strong dominant lead that is the opposite of your place on the scale, and giver her the space to balance you.

Recognition and credit — Make sure to recognize both risk-taking visionary efforts, as well as excellence in planning and execution. Most important — allow for failures, and even celebrate the ones made in good judgement, and with big effort.

Last but not least: all the reviews and goals mentioned above are not in contradiction to agile, lean, and other flexible development methodologies. I have worked in teams which were at the bleeding edge of agility, yet still used a similar framework (though I highly recommend to keep the reviews themselves agile and lean — avoid people spending precious time on beautifying slides). Also, quarterly and annual goals don’t mean quarterly and annual deliverables — launch and iterate early and often. Walking the tightrope is all about the balance.

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There is definitely more than one way to skin a cat, and many more to do “product management”. In no way do I think that my way is the right one, the best one, nor do I even have a single way of doing things. My intention in this and subsequent posts is to share some product management challenges and dilemmas I faced in the past, which I hope professional Product Managers, as well as anyone interested in the field, will find useful and engaging.