Roadmaps ahead can be deceiving… Trust is built on your ability to tell the story of the journey behind you.

In my experience, wearing a variety of project and product management hats, it’s very easy to be distracted by exciting experience designs, new feature releases and fighting fires. When the going is good… and busy… things like decision and risk logs, formal contract addendums, and the ceremony of recurring status updates can get skipped. It’s easy to assume everyone participating is actively aligned, particularly when there’s a “sky is blue” vibe and everyone appears to be in step and running toward the promise of a North Star roadmap. 

As a result, one of the common sources of breakdown in a client-to-engineering team relationship is the lack of rigor around routine communications and checkpoints to assure we’re on track.When we least expect it, the need to tell an honest and compelling story of how we got here can arise at any moment. Totally possible a new c-level or VIP will join the stakeholder group with new perspectives and opinions, and it’s natural for resources to come and go on any product or engineering team over time. 

Whether a team is iteratively working “agile” or not, asking how we got here is a fair and critical question that everyone contributing to a shared mission should be comfortable asking and answering with confidence and clarity. 

Knowing how we got here is powerful! It sets the stage for making the right-next-best-step decisions together. It’s a trust builder like no other in this business. It’s proof that doing what we said we were going to do matters.

It gives insight to:

• Our ability to calculate ROI for the business paying the bills and making the investments

• Costs and timeline expectations for future efforts

• Key learnings and decision points along the way

• Roadblocks and how they were overcome (or how they are still impacting the team’s ability to deliver)

• How real life turned out versus the original happy-path plan

• How decisions led to savings or losses

I have seen many times where this question has brought a lot of discomfort and finger pointing.

The kind that results in dumpster diving into backlogs, taskboards, invoices, emails and meeting notes. But I’ve learned a proactive engagement setup to keep tabs on how we got here that can enable an easy, energetic and productive conversation when the need arises.

Here’s how to set yourself up from the get-go:

1. Clear contracts with budget guardrails by objective.

If the contract isn’t specific to what’s going to be built, then it needs to be specific to how it’s going to be achieved.

What processes will be followed, how will solutions and decisions be documented, and who owns and maintains access to all of the work products (designs, docs, toolsets, code repos, infrastructure, etc). There also needs to be a clear set of objectives or milestones with declared budgets for each. Understanding these guardrails and returning to them regularly to align work in progress and next-step decisions to the core objectives is key to a healthy relationship. 

In cases where you don’t have a formal contract because you’re working within the same organization, written working agreements are a great way to capture commitments and expectations between stakeholders and those they employ to make things happen. 

2. Central tracker for high-level deliverables and reliable status that aligns into your agreed objectives.

You don’t need fancy software (of course it helps to have apps like Jira and Azure DevOps), but what is key is capturing a rolling tally of what is promised and what is delivered on a weekly basis. Bonus points if you include when the client or stakeholder has reviewed and approved the outcome; thereby creating a method to capture the associated costs of each delivery increment. These increments can be by sprint or by week or by feature, and I recommend asking your stakeholders what’s important to them for visibility and business ROI reporting. Then stick to it!

3. Establish a central decision and risk log.

These can be solved with project management Saas apps, but a spreadsheet will also do as long as it’s easy to access and maintain for reference. Include material decisions that could impact the quality or performance of the product or the engineering effort. Your log should answer these questions: Is an originally planned core feature being deprioritized for a new learning? Are decisions being made to build new enhancements when your engineering team is asking for time to harden the infrastructure? Is a decision to pursue additional rounds of refinements of a capability going to lead to overruns for any budget or time guardrail for a core objective?

For each entry in the log, describe the situation, link to task boards where helpful, capture the decision and date, who made the decision, potential impacts or unknowns. Include a method for the stakeholder who is accountable to the business to sign off to acknowledge the decision. This is a critical step to ensure alignment and ownership. It can be as simple as a comment in a shared document.

In the event you need to go back and find out where critical pivot points were part of your journey, this information is priceless! If it’s incomplete or not maintained in a routine cadence, it’s worthless. 

4. Establish a recurring communication loop with an easy snapshot report.

Create a simple document template that captures the high points that are easy to understand by someone who is not technical or close to the daily happenings of the product and engineering team(s). It should not take more than 15 minutes to craft each week or 5-10 minutes for a recipient to review. Include recent wins, blockers, risks, decisions, and how the group is tracking on budget and time guardrails by core promises and objectives. Provide links to details or task boards for those that seek more supporting documentation to your status assessment. 

If implementing this step feels overwhelming, hop on a free consultation call with us so we can share how we can help you design a template and supporting workflow that’s right for you!

5. Align time tracking and invoicing to core objectives (or outcomes).  

This is essential for third party vendor-partner relationships and I’ve seen this opportunity missed by inexperienced teams. It may be discussed more frequently during contract negotiations and renewals, but how well a product or engineering team adheres to the budget guardrails and respects the limited and precious investment dollars granted by stakeholders matters every day! 

Sure, what we budgeted versus required in real life to tackle an issue is going to be higher or lower than planned. It was always a good faith estimate. Not knowing by how much is a real problem and indicator your investments may be mismanaged, and your future decisions more likely misinformed. 

6. Resist the temptation to go above and beyond.

Delight your clients by doing what you say you’re going to do. No more, no less. There are plenty of surprises in product development related to outcomes and unexpected roadblocks already! In my experience, going above and beyond at the expense of time or financial cost to the stakeholders is not a welcomed surprise, particularly when there’s other high priority items underway. Yes, some of the best ideas are sparked by the engineering teams closest to both the problem and the solutions. But when the investments are made toward these innovations are business decisions that need to be made and owned by the stakeholders, acknowledged in your decision log, and noted in your snapshot loop report as a win! 

Once this structure is in place… (and I cannot stress this enough) maintain it with intention! 

Be sure everyone on the team can access and answer how we got here with ease and clarity. 

Proactively communicate and celebrate the wins, losses, twists and turns of the journey and show you’re using the past to make better decisions into the future.

Over time, trust will grow with each next step of your journey ahead. 

What happens if you don’t have this kind of structure in place? Are you curious if you are part of a well-managed engagement?  

It’s ok! Start. We help both product engineering teams and companies who hire them implement these kinds of healthy structures and practices to get and keep on track with their technology and product development investments.

Can’t wait to connect and to be able to tell you more about how we can help.

Let’s  schedule a time to talk more about digital product & delivery or email us at hello@devsio.com to get the conversation started.