Template for Building a Winning Delivery Process Between Commercial and Product/Engineering Leadership

In a fast-moving B2B organization closing big deals, a legacy organization improving agile or, a fast-moving startup with critical features on the horizon the issue of aligning engineering investment, roadmap delivery dates, and missed expectations can quickly spin out of control.

Between commercial, product, and engineering leadership, a potential anecdote to rebuild trust and transparency can be instituting a simple, scheduled Product Steering process.

To rollout a Product Steering process, the leadership team collectively needs to follow these short steps:

Steps to Sustainable Product Steering:

1. Align on a Win-Win Agreement

2. Align on Process for Roadmap Prioritization and Execution

3. Execute (with updates and openness)

4. Repeat on a Scheduled Cadence (either monthly or quarterly, depending on business need)

Step 1: Align on a Win-Win Agreement

Overall, all three parties have NEEDS. Without all parties having their needs met, one party will tailspin in a lose-win environment.

• Commercial NEEDS delivery dates they can trust;
• Commercial NEEDS the ability to be flexible with the sales cycle, new contracts, and partnerships;
• Product NEEDS an agreed-upon process for understanding commercial objectives (i.e. increased revenue) while balancing priorities for tech debt and ProdUX debt;
• Product NEEDS time-based roadmaps to project plan, coordinate and execute user-centric product activities (interviews, UX testing, design, etc.)
• Technical NEEDS flexibility to provide estimates that can be revised after more detail in grooming (see Cone of Uncertainty)
• Technical NEEDS a process for updating delivery commitment dates as priorities change (see Resteer Process below)
• Tech NEEDS systematic planning to avoid Software Death March Deliverables that sacrifice engineering morale, room for growth, and reputation preventing recruiting top talent.

So, what can all of you guys do to get what you need? Establish a repeatable process to reinforce trust via Product Steering. To help get you started, here is an example Product Steering and Capacity Template to customize.

Step 2: Align on Steering Process for Roadmap Prioritization and Execution

Step 2a: Align on Format, Timing, and Prep Materials

Format and Timing:

1. Decide on the timing together. Depending on how fast the business is moving, the types of things you are building, and size of the engineering team, decide on a monthly or quarterly cadence — no smaller. (We are talking features/epics here, not user stories, bugs or a column on a report.)

2. Decide on the tool. Engineering may want JIRA/DevOps epics, Product may want Trello, and Commerical may want the easiest thing that they can quickly understand between meetings. Decide together what is best for the three groups to access and plan. (Note: for the scope of this outline, we will use the Excel Template linked above.)

Preparation Documentation for Steering Meeting

1. Engineering to provide the capacity of the team for feature work. When providing capacity, be transparent about an allocation % needed for tech debt, % allocation needed for PTO/sick time, and % allocation needed for ad-hocs/fixes. Based on objective data and expert estimates, adjust the formulas as needed:

2. Product complete list of feature intake from Commerical, Operations, Engineering, etc. with as much detail as possible for planning and estimation. Where possible include links to wireframes, JIRA epics, etc. to help with estimation.

3. Engineering provides low and high estimates (in-person weeks) based on the level of detail and design (see Cone of Uncertainty), as well as additional comments for bigger risks and consideration. Please note, if your engineering leads are uncomfortable with this process, please revisit the agreements above.

Step 2b: Execute Steering

• In the Steering meeting, there MUST be an empowered representative from each area. If they cannot be there, be ruthless about rescheduling.
• To conduct the meeting, (1) start by aligning on how many weeks are available for the period for prioritization, then the engineering lead will review the remaining amount of work on carryover features, followed by the product lead reviewing the draft prioritized list of all features.

• After setting the context, have hard debates on what priorities should be. Move features in and out of the period until the prioritizes features DO NOT exceed capacity. See example of moving features to total capacity:

Note, not everyone will be happy, but you must be ruthless about leaving the meeting with a commitment (i.e. discuss Disagree and Commit before the meeting). If you cannot get to an Agree and Commit or Disagree and Commit, then either schedule a follow up or this is an investment issue that needs to be escalated to the budget authority to invest in more engineering (contractors or FTE). Steering is about economics, not about people magically delivering more than the 100% they are already giving or the company is investing.

3. Execute (with updates and openness)

• After the grooming of epics, product to provide a public updated roadmap to all stakeholders.
• Each month, engineering to provide updates on each feature process to mitigate risks.
• If an event arises where the plan must be changed within the month or quarter, the team will come together to (1) Resteer and (2) Engineering provide new dates.

Resteer Scenario Examples:

Commerical, “We just signed a big deal and a I need these features within 60 days.” Product, “Our current priorities are set for the quarter. Can this client wait until next quarter or should we resteer? If we need to consider a resteer, I will schedule the group and get new estimates.”

Operations, “We are scaling must faster than we thought and support is dying over here with manual tasks. Can engineering work on X — ASAP?!?!” Product, “Here is our current steering list of candidates for next quarter, can this wait until then or should we resteer?”

4. Repeat on a Scheduled Cadence (either monthly or quarterly, depending on business need)

This process is as good as the people and trust between the business lines. Each quarter, look for opportunities to improve the tools, measurement, agenda, etc. to continue to serve the needs of all three parties. Most of all, trust is built by saying what you are going to do and then doing it.

• Commerical is responsible for following the planning and prioritization process.
• Product is responsible for intake, collaboration, design, and transparency.
• Engineering is responsible for hitting deadlines committed to and raising risks as they get further into the details vs. their capacity.

Good luck!

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Kirby Montgomery is a post-it note advocate, a coffee glutton, a practitioner of data & design user-centric problem solving, and an extreme prototyper. As an executive product leader at Rethink First, he is on a mission to help parents of children with disabilities navigate the world of pediatric therapy and impact product delivery in the broader mental health ecosystem. He is also a contributor to Product Coalition, a startup advisor, and a former executive product leader at MSTS Fintech (acquired by Corsair Capital).

If you want to chat about any of the ideas presented here, please feel free to reach out via LinkedIn or guykirbymontgomery@gmail.com.