What activities do you do to help set expectations between development and upper leadership?

For a visible project that has the attention of upper leadership, I think of 3 checkpoints with leadership:

1. Showcasing the vision at the beginning of the project

Once I have nailed down the problem to solve, why it's important to solve, how it contributes to broader business goals, and you have an idea of how you want to solve it i.e. conceptual mocks - I present the vision for the project to get alignment with upper leaderships. While I'm getting this ready, I will make sure to keep my manager and other key stakeholders in the loop to get their feedback and refine the vision. 

2. Reviewing detailed designs that we plan to implement

Once I get feedback from the vision, we incorporate them into the designs that we plan to implement. Once we feel confident in the designs that we want to implement, we do another review to make sure leaderships understands at some level of detail what will actually ship and when. 

3. Weekly updates on project progress

Once we're aligned on the detailed designs and start building, we send out weekly updates on our progress. This allows leadership to chime in if clarification is needed. 

Note: If at any point there's a major change in the product direction because of new information, I make sure to communicate up to leadership and schedule a meeting if needed. 

4. Feature has shipped and measuring impact

I make sure to communicate timelines on when the feature will ship and when it shipps, I make sure to emphsiaze in our update that the feature has gone out the door and is in the hands of users. Also, I try to follow up a few weeks or a month later with metrics that show the impact of the feature. 

Communicate, communicate and communicate more!

We have a quarterly product strategy meeting where the PMs share their plans and the execs ask questions ahead of the work being done, so there's time for the PMs to go back with the engineers and designers to refine based on any course corrections.

We keep a set of artifacts available - a product roadmap and a product staraegy doc that have the details of what we're working on. We document a lot of our conversations in Notion and these are available for anyone in the company to read.

Setting clear and realistic expectations between development teams and leadership is key to the success of any product development team. Here are some strategies I use to help set expectations effectively:

1. Clearly articulate goals, timelines, and challenges. Regularly update leadership on progress and any deviations from the plan.

2. Ensure that development goals align with the broader business objectives. Help leadership understand how the development work contributes to the company's overall success.

3. Establish and communicate OKRs and KPIs that both development teams and upper leadership can use to measure success. These KPIs should be tied to business outcomes, for example: product adoption, customer acquisition, retention, satisfaction, and financial impact.

4. Provide regular status updates and reports on progress.

5. Proactively identify and communicate potential risks that may impact timelines or outcomes. Offer mitigation strategies and contingency plans.

6. Involve leadership in key decision-making processes. Seek their input on strategic choices and keep them informed about major decisions.

7. Establish regular feedback loops between development teams and leadership. Encourage leadership to provide constructive feedback on progress and be open to adjustments based on their input.

8. Celebrate achievements and milestones! Share success stories and demonstrate the impact of development work on the business.

By using these strategies, you can create a culture of transparency and collaboration, ensuring that both development teams and leadership have a shared understanding of expectations and are working towards common goals that are tied to business outcomes.

“Managing up” is core to being a successful PM given how front and centre product development is for a business to grow.  “Communication with the right level of detail” is key to making these communications meaningful. When communicating, expectations need to be set both in terms of projects in flight as well as new opportunity areas as they surface up. 

For projects in execution: 

1. A progress check in in how the committed projects are progressing - this can be a monthly discussion forum so there is an opportunity to discuss open questions (avoid making this is a FYI meeting, rather create space for discussion) or a newsletter of sorts sent out on a bi-weekly/monthly cadence across your product portfolio for offline reading. 

2. If it is mainly to keep one person updated, have a running document of updates so that the/she can refer to as needed. 

When it comes to new opportunities, some guiding principals when engaging with your leadership: 

1.  Once you have something meaningful to share along with a open question or an approval from your manager, schedule a “discussion” time with your leadership. 

2. As an IC PM, target having these periodically throughout the year or at the least, for large initiatives leading to your planning cycles. These help evangelize your concepts with your leadership.

Be transparent and over-communicate. Clear expectations between development teams and upper leadership are crucial for alignment and stakeholder satisfaction.

1. Establish a Communication Plan: Set a schedule for project status updates and adhere to it. Keep updates concise and actionable. If there are risks to the schedule with mitigation plans in place, communicate them upfront. When needing leadership intervention or decision-making, request it directly.

2. Actively Seek Feedback and Alignment: Request feedback from upper leadership on project direction, priorities, and performance. Transparently communicate project risks or concerns, as their decisions may differ from assumptions.

3. Be Transparent: Never withhold or sugarcoat information. Openness enables effective problem-solving and decision-making. Upper leadership's role is to support and remove obstacles, which requires awareness of issues.