“Learn to fly with broken wings”

Assaf Miron
CyberArk Engineering
5 min readJan 5, 2021

As a product manager you are expected to own the product vision, while the developers are expected to turn that vision into a reality. Simple, right?

But what makes a good vision? Like every PM you wish to have a vision that is worth realizing. But most importantly, how can you keep your vision intact despite reality?

Facing the reality

You were asked by your manager to develop a roadmap for the upcoming year.

Getting into gear! Developing the roadmap

  • You have the data (or collect as you go)
  • You “get out of the building” to meet customers
  • You validate some of your ideas
  • You share your thoughts with stakeholders (R&D group managers, product owners, customer success…)
  • You know exactly how to go from point A to point B and the value for your customers

You rock!

Now it’s for a reality check, After talking to the product development team, it seems that things are more complex than anticipated.

Broken Wing Images | Free Vectors, Stock Photos & PSD

You are an experienced PM and knew that could happen, so you adjust the plan, taking some “nice to have” content off the roadmap for now — just a “slight dent in the wing” you say.

After a sprint or two you learn that another project or initiative came in that requires more resources. It is affecting your plans — not to worry, just make some more adjustments (the UI can be almost pixel perfect for the first release, maybe not all content is a must).

Getting closer to the first release and things get complicated, no one could have anticipated this…

You try to make some compromises (who needs a “cancel” button anyway?!) — “yet another dent in the wing”.

We’re flying through an air pocket — hold on tight

You will probably get a few dents in the wings.
Your spirit may be broken at times.
You must learn to fly with broken wings.

You know that this roadmap is what’s needed at this point, for the next year.
Yet, as times goes by, things seem to be getting further and further away.

I’ve had this feeling more than once in my career.

At times it really broke my spirit. I won’t lie, it’s tough.

But every time, even when it took days, I reminded myself of the benefits that are awaiting at the end of the road and getting to the customer value I planned — keep flying.

Let me share my secret with you — keep your focus.

Keep your focus

Given that you do know your customers, given that you did the right validations and know what would benefit your customers — be certain of yourself.

All of the validation you’ve done might be just what you need to convince the product development team, management and most importantly — yourself!

You are on the right path, don’t lose sight of your vision.

As long as you did your homework and you have that vision in your mind, don’t let it go.

It’s OK that things don’t always go according to the plan, you just need to be aware of the path.

I Love It When A Plan Comes Together

Plan the first milestone in detail

Think of the goal of this milestone. What are you trying to achieve?

  • Define different use cases that solve small user problems.
  • Prioritize these use cases. These will be the core values of this milestone.

The top 3 use cases will be your “must haves” that the product team should begin solving; the others can be “nice to haves” that you can live without if something needs to be cut out.

  • Determine what kind of feedback you plan to collect from this milestone
  • Decide on the validations that you’ll need to do
  • Understand what the value of this milestone is to the customer?

Thinking about this could help you drive forward the next milestone, with verified and validated answers to your questions. Having this could give you assurance to be bolder in the next milestone, aiming higher.

  • Determine how you are going to monitor / keep track of in this milestone
    Would that be customer usage?
    Would that be convergence?
  • Define how you are going to collect this information and use it as evidence

Going through this exercise “arms” you with enough data to be very sure that you are on the right track. Get ready for your next stop, the next milestone.

Plan the second milestone at a high-level

Similar to the first milestone, you should begin with the goals.

Thinking about KPIs for measuring the goals of this milestone.

Define anchors for this milestone — what are the things you can’t do without? What are the things you need for better validations?

Since you should start planning the second milestone not long after executing the first one (sometimes even before it is out), keep track of the decision points that you will measure and validate during the first milestone.

Once you have the data from the first milestone you will know the answers to all of your open questions. Don’t be afraid to leave some open during this phase.

You can keep things at a high-level, no need to drill down into details.

Your anchors should be your “vision guardrails”, don’t give them up.

When in doubt, hold your altitude. Nobody ever collided with the sky.

Make sure your milestones set the course to your future destination

Always think of the future and understand that it’s OK if your milestone goals did not go exactly according to plan.

What is the next step? Are you headed in the direction you set for yourself? Are you any closer to realizing your vision?

If you prioritized right, kept your anchors, and planned your milestones, you should already be halfway through with the most important items on your list. Keep making sure to focus on the path to your vision, your roadmap.

This way, even if things go south your compass is still pointing north.

You should remember, “no matter what happens, fly the airplane”.

How about you? How are you keeping focus on your roadmap?

The title was inspired from the song Across Waters Again by Blindside

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