In the middle of planning

There are many books about planning and project management, including mine, but few describe how to deal with planning, from commitments through completion, as a middle manager. Perhaps you prefer top-down planning or bottom-up planning. Either way, as a middle manager, you get smacked between both.

How do you create a plan that pleases the management chain above you, the staff below you, and your own desires for influence and impact? Is that even possible in one lifetime? Yes, not only is it possible, it’s also fast and easy. You just need to stop thinking about a single plan and start thinking about three different interlocking plans: a stakeholder plan for their current planning period, an 18-month balanced plan for your team, and a regularly reprioritized team backlog.

I know having three kinds of interlocking plans sounds more complicated than having a single plan that works for everyone, but using a single plan is far more difficult and time-consuming. Why? Because stakeholders’ needs are different from the needs of your staff. Stakeholders need a plan in their prescribed vernacular and format that aligns with their latest thinking. Your staff needs a simple backlog in plain language with continuity across planning periods. And you need a plan that captures everything and easily maps to your stakeholder plan and to your team backlog. Let’s reveal how to create all three interlocking plans with only a week’s worth of effort.

Word from on high

Planning typically starts with edicts from upper management and partner teams. Maybe you are included in drafting or reviewing those objectives (called OKRs at Microsoft) and their associated work items. Regardless, your group is expected to deliver them, along with estimates and timelines.

Your group likely has multiple stakeholders: your manager, your director or VP, and the leaders of each of your partners. Usually, different stakeholders don’t care about each other. They only need details about work you’re doing for them unless other work negatively impacts them. They also want your plans to be aligned with their different planning documents, milestones or sprints, and tracking tools. That’s another reason why a single plan doesn’t work.

Your role as a middle manager is to accept all stakeholder requests, share them with your group, come up with rough estimates, prioritize the work, and respond to each stakeholder using their planning documents, milestones, and tracking tools. As I mentioned, you can do that in a week (details shortly). Afterward, you can work through any conflicts or concerns across stakeholders and adjust your plans accordingly.

Better learn balance

Naturally, you get far too many requests. That’s okay. Create a list, including which stakeholder requested each item, and share the list with your team. If you manage multiple teams, only share the items applicable to each team.

Accepting, listing, and sharing the items can be done in 30 minutes. The key is not to push back—that’s exhausting, time-consuming, and counterproductive. Just accept all requests, list them, and share them with each team. Make it clear to your group that they won’t end up doing everything—they never do. The job right now is for each team to brainstorm every high-level item they want or need to do over the next 18 months, including their list of stakeholder requests and reductions in technical debt. The result becomes each team’s 18-month plan in the form of a McGrath and MacMillan Options Portfolio.

An options portfolio is a two-dimensional grid. The grid’s vertical axis shows increasing execution risk (technical or operational), and the horizontal axis shows increasing market risk (customer or competitive). The lower left corner holds current core work (e.g., live site support). The middle holds the expanding items that define the next release. The top edge holds positioning items that customers want but are hard to make. The right edge holds scouting items that are easy to deliver but customers may not embrace. And the upper right corner holds game-changing ideas. Each team places its brainstormed high-level items in the appropriate grid location. They can format this as a table in Microsoft Word with a glossary that defines each high-level item.

For a balanced portfolio, your team’s work should spread across all portions of the grid—not enough core items and your current business suffers; not enough expanding items and your customers will reject your next release; not enough positioning, scouting, and game-changing items and you’ve got no future business. Creating a balanced portfolio typically takes between two hours and two days, depending on how each team goes about brainstorming.

For your consideration

After your teams finish brainstorming, you should review each options portfolio with its team. These review meetings typically take an hour. Start with the core items (lower left) and work your way to the game-changing items (upper right). Ensure you all agree on what each item is, who it’s for, and its risks. Add more items as they occur to you or the team, especially if they fill gaps in the portfolio.

There are three additional considerations to focus on during your review.

• Underline the items that are genuine commitments (e.g., live site support). These are the items you prioritize over all others and are certain to achieve in the current planning period. Together they should consume no more than 30% of the team’s capacity during that period (anything more will compromise that certainty). Emphasize to the team that underlined items matter most and come first. Everything else is best effort.
• Being clear about your genuine commitments and risks helps your team account for issues that arise, but planning for success is also important. What if some items are wildly popular? What’s needed for scale? How might priorities change? Help your team think the plan through.
• Ensure you know how to measure each item’s impact. Sometimes the impact is enabling new scenarios. Sometimes it’s greater revenue, higher engagement, or lower cost. Regardless, you’ll all want to know what you should highlight at review time.

You tell your boss

In just half a week, you’ve got an 18-month plan for each of your teams. Those plans contain more than enough items for you to fill out quarterly, six-month, or annual stakeholder plans. (Microsoft orgs typically do six-month planning.)

First, create a list of all the underlined items and a desirable collection of the expanding items for the current planning period across all your teams. Also select interesting items from the outer edges of each portfolio. Then create estimates for each item in your list. For the rough level of accuracy needed at this point in planning, I prefer to do quick t-shirt costing with each team’s tech lead (which typically takes an afternoon).

The items and their associated stakeholders, teams, costs, and priorities go into a table. Underlined items are pri 1, other core and expanding items are typically pri 2, and remaining items are pri 3. I like to put this table in Excel, especially if I need to draft different plans for different stakeholders. That way, Excel can automatically compute item delivery dates based on estimates. Excel filters and pivot tables can also produce the various lists, tables, and tracking-tool uploads each stakeholder desires.

All that’s left to do is write some prose summarizing your group’s work for the planning period and copying the various Excel-generated lists and tables. If a stakeholder wants a cut line, place the line in front of that stakeholder’s first item whose delivery date exceeds their planning period. (No worries, you can reprioritize as needed later.) Also use Excel to generate each team’s associated backlog. That’s two days of work at most—all your planning done in a week.

I got a backlog

By now, you’ve noticed that it’s nice to have 18-month options portfolios for each team because they provide a handy way to create plans for each of your stakeholders, even if those stakeholders use different planning periods and rely on more than one of your teams. These balanced portfolios also help retain engineers and innovate your products, because they include long-term cutting-edge ideas.

Even more importantly, 18-month options portfolios span planning periods, facilitating continuity and generating pride. Each time you go through planning with each of your teams, you update that team’s options portfolio. Team members get reminded of long-term plans and celebrate the surprising amount of work they’ve completed. (Portfolios fit on a single page, so you can see it all at once.) The team’s backlog gets refreshed with new and familiar items, and team members get reinvigorated with new challenges and continued progress.

That was easy

It’s tough being a middle manager caught between bottom-up and top-down planning. However, you can create a plan in a week that pleases the management chain above you (and partners), the staff below you (including multiple teams), and your own desires for influence and impact. (The process often takes two weeks due to meeting schedules, but that’s far less than the two to three months of planning many groups endure.)

Start by sharing the list of all your stakeholders’ requests with your teams, acknowledging that you don’t expect them to get everything done during this planning period. Have each team brainstorm all the high-level items they want or need to do over the next 18 months, including their stakeholder requests and technical debt, and place those items in an options portfolio. Review each portfolio, filling in gaps, underlining commitments with top priority, preparing for success, and knowing how to measure the impact of each item. Then apply t-shirt costing to create an Excel table containing all the underlined items and enough other items to fit into the current planning period. Use filters and pivot tables to produce all the various lists, tables, and tracking-tool uploads your stakeholders desire for their plans, as well as the backlogs for each of your teams.

These steps result in customized plans for each stakeholder; clear, consistent, and innovative 18-month plans and aligned backlogs for each team; and opportunities for you to assign work, influence direction, establish scope, and prioritize focus for your group—all with only a week’s worth of effort. What will you do with all your extra time as your peers slog through months of planning? Here’s an idea: Plan a vacation.