Shepherding

Other than dust bunnies and hairballs, no product is made in a vacuum. Product success takes a herd, but we must first align the sheep.

Many product decisions can go in circles, which is frustrating and demoralizing for anyone involved. The uncertainty leads to wasted time and inaction because stakeholders aren’t rowing in the same direction. There’s an alignment problem.

A great product manager knows how to shepherd their stakeholders to align on a clear decision.

The Good Shepherd

Misalignment happens when people have opposing viewpoints on a topic. These differing perspectives could be simple misunderstandings—people wanting the same thing but using different words—or fundamental objections. Regardless of the source of the misalignment or whether there’s misalignment at all, people want to be part of the decision-making process.

I use a six-part framework to drive stakeholder alignment: Shepherding.

1. Externalization
2. Stakeholder Mapping
3. Individual Alignment
4. Group Alignment
5. Signoff
6. Immortalization

Before elaborating on the six stages, let’s unpack the ethos of shepherding. The spirit is to drive what’s best for the business, not to satisfy our career goals, some executive’s agenda, or political maneuvering.

We must believe that teams are strongest as a unit—a dispersed herd of sheep moving in scattered directions will accomplish nothing. A shepherd does not force sheep to do anything but seeks to get them moving in one direction that supports their interests.

We must respect the individual’s intelligence. In the knowledge sector, influence—not control—is essential. We must bring people along for the journey to ensure they feel seen and heard in the decision-making process.

Shepherding takes significant time and effort (often 3-4 weeks), so we must only invest in one-way door decisions that impact multiple areas of the business: launching or deprecating critical features, major system upgrades, or new policies and programs.

Step 1: Externalization

The first step of shepherding is to externalize the idea into an artifact, such as slides or a document. I prefer a document because putting ideas into writing helps sharpen thinking and provides adequate detail for stakeholders to review offline. Slides are easier to create, but they’re insufficient to convey ideas without a verbal presentation.

A culture of writing—materializing ideas into prose—helps others assess a proposal objectively and read it asynchronously. Most importantly, a written artifact ensures the idea prevails over personalities and prevents the loudest voice from domineering the group.

Aim to keep it under two pages and place supporting data and materials in an appendix.

Step 2: Stakeholder Mapping

Determine the stakeholders that need alignment. Most product decisions will include other product managers, executive leaders, and functional representatives from engineering, customer support, sales, marketing, and operations. Catalog these stakeholders at the bottom of the proposal document. Most decisions will involve 3-4 stakeholders at minimum, to a dozen at maximum.

Ensure to list individual contributors most impacted day-to-day by the decision’s outcome. Leaders will look to them for guidance when they ultimately sign off on the proposal.

Step 3: Individual Alignment

With the written proposal and stakeholder map in hand, seek individual feedback. I recommend meeting with each functional group separately but no more than 2-3 at a time to keep the discussion focused and intimate. Seek their feedback, listen to their concerns, and aim to address their objections in edits to the document.

In these discussions, it’s essential not to get defensive but to seek understanding. Press the individuals to offer solutions to problems they present—even if these ideas are not implemented, voicing them can unravel concerns that aren’t valid.

Step 4: Group Alignment

After meeting with everyone individually and incorporating their feedback to bolster our argument, arrange a group review. Share the document in the invite 3-5 days before the meeting and instruct everyone to pre-read and leave comments. We can then begin the group review with the comments to keep the conversation focused, as it’s easy for people to derail these meetings with tangential topics.

The good news is that everyone should be mostly aligned by this meeting. The group session may feel like a formality, but that’s good. Like a wedding, the group review is a public endorsement that everyone present supports the decision being made. They may disagree with it but respect it nonetheless since they were consulted on the topic.

Step 5: Signoff

After the group review, add a signoff table at the bottom of the body content before the appendices. I recommend three columns: the signer’s role, name, and signoff date. To “sign off,” the stakeholder should type the date beside their role and name.

Getting signoffs will require tactical shepherding. After the review meeting, send a follow-up email thanking stakeholders for their participation and requesting they sign by a specific date. I recommend a deadline of 2-3 days away.

Some people will sign off promptly, but others will need chasing. Don’t let the discomfort of pestering people prevent their signoff. If people haven’t signed within two days of the first request, prod them with individual messages. Another tactic is to reply to the original email. Keep pending signers on the To: line, move all other stakeholders to CC, thank those who have signed, and gently request others to do so.

Step 6: Immortalization

After everyone has signed, rejoice, for we have made a complex, business-impacting decision across multiple functions! To immortalize the decision, send a final announcement to all stakeholders confirming the outcome. Thank them for the feedback, ideas, and support. Emphasize that it was a group effort and that they should feel like co-owners.

It was no small task, but we have shepherded the herd to greener pastures.