December 1, 2022
By: Adam Beebe, Rev Ops Architect
If you scroll the RevOps hashtag on LinkedIn, odds are every other post is going to say something to the effect of “Rev Ops deserves a seat at the table” or “Tired of being swamped in tasks and want to be more strategic? Prioritize!”. That’s all fine and well, but rarely do these posts answer the question of how. Hopefully, this guide will give you some sort of framework for effective prioritization that works for you and your organization.
Defining the Challenge
But before we get too deep into things, let’s set the stage. Imagine, you’re in your first team lead role of a lean Ops group - it’s you, maybe 2 others - at a Series A or B startup in hyper growth mode. You barely have time to eat lunch most days because of the volume of ad hoc requests. The new lead routing process you designed is 2 weeks behind schedule for release. Customer Success has a new PLG tool they want integrated with Salesforce for product insights. Marketing is updating the fields on a demo request form and changing the MQL score threshold. It’s month end and sales reps are coming to you for deal assistance. Oh, and its board deck season. PTSD flaring up yet?
How do we end up in this situation? It can be easy to finger point at specific issues like tech debt, or changes other teams made without conferring with you. But what could you have done to prevent those decisions from affecting you? How can we as Ops spread these issues out so we aren’t always drowning? Spoiler alert, we can’t. At least not entirely. What we CAN do is attempt to control our own destiny by laying out a prevention plan, otherwise known as a roadmap. Now if you’re already in fire fighting mode it’s easy to dismiss a planning session, but those fires will just keep coming. As the old saying goes, the best time to plant a tree was 20 years ago; the second best time is now. So let’s get planting.
Before we get into the long term planning structure, there are a few tools I’ve learned over the years that have been extremely useful in stack ranking initiatives.
A handy tool that’s unblocked me countless times is the question “What is the business impact?” It can be used out loud in conversation, or as part of your internal dialogue when deciding what to do next on your daily task list. Posing the question directly to a colleague may seem abrasive, but in reality it forces the requestor to evaluate the authenticity of their ask. Suddenly that new checkbox doesn’t seem so important if a report suffices. In that instance, not only will this reduce your short term load, but helps prevent any missed expectations. Applying it to your long term initiatives can aid in any ROI conversations with leadership. If you think about the impact as being ‘degrees of separation from revenue’, it gets easier to assign at least a ballpark dollar figure to any line item on your roadmap.
The second is the Eisenhower Matrix. It’s a decision making framework pioneered by President Eisenhower. It’s more useful for daily to weekly planning, but things that routinely fall in the ‘Decide’ quadrant may be good agenda items for your quarterly planning. They may just need a second set of eyes to affirm priority, or maybe there are some pre-requisite projects that need to be prioritized before accomplishing them. If it worked well enough for Ike to get the interstate system rolling, it should suffice for RevOps.
Now that we have mechanisms to help with establishing priority, and you probably have a list of things in mind, let’s get into some tips for setting a quarterly roadmap.
Get the right stakeholders involved. The group will look different for every org depending on reporting lines, but generally start with functional heads. Sales and Marketing leaders, COO, a Finance representative, and perhaps someone from Product. You want to keep the room tight, but not exclusionary.
Establish a cadence. For operating on a quarterly roadmap, monthly should be more than enough. The first meeting probably needs to be at least an hour and should be focused on getting executive buy-in on the roadmap you present. The second is a shorter meeting to check progress and update priorities if needed. The final touch point in the cycle should be a post mortem, plus a preview of the next quarter’s roadmap.
Come prepared and advocate for yourself. Here is a template that, in some capacity, has worked well for me. Feel free to make a copy and modify it to suit your needs. Spend time with your team and interviewing other stakeholders to have this filled in prior to the first prioritization meeting. Ops is often in a unique position to feel a lot of the business’s pains before they roll up to the executive level, but we’re not omnipotent, so be prepared to field questions about your judgment calls. Sometimes there will be initiatives you have to take on that you didn’t expect, but it’s fair to ask for justification. This whole process should be a conversation, not any one party dictating.
Shift the burden. Make sure that everyone else is aligned so that when urgent requests arise mid-quarter, you can let leadership go to bat for you. Similar to the business impact question, if someone has to suggest to the COO that their thing is more important than everything else on your list, they may back off. Or not, but it’s then up to the leadership team to make that call, not you.
Know what to drop. “We’ll deal with it when it happens” isn’t really acceptable. If there are 10 things on the roadmap, make sure there is agreement on what work would get paused in the even of a mid-quarter emergency. This can be a difficult conversation, but it’s important to push for an answer.
There are tons of benefits from going through any prioritization exercise, but one of my favorites is having something to point to when new things come up. In a scrappy startup, sometimes we just have to let things burn. It’s hard, but if it wasn’t on the list at the beginning of the quarter it may not get done.
The final piece of advice, if you can call it that, is around communication. Even if you’ve created the perfect roadmap, it’s useless if nobody understands the value. A key component is conveying ‘The Why’ behind any initiative. For any exercise, ask yourself “how does my audience communicate?”
Learn to speak their language. Think about it like this, who are the people they (in this case, senior leadership) answer to? Board members and VCs.
Don’t get too technical. Tying back to the previous point, high level bullet points and dollar figures are what matter. If you’re like me, you may have a tendency to go deep in the weeds and spend too much time on technical aspects. In a prioritization conversation, try to avoid this unless it’s specifically asked. Paint in broad strokes; you want directional sign-off, not agreement on a field name.
Connect the dots. Do your best to illustrate how each line item affects the people in the room. If they have to do this for themselves, the conversation may drift and you may leave the meeting without the answers you need.
Prioritization is not always going to be cut and dry. You may go through this exercise only for it all to get tossed out the window a week later because of something nobody saw coming. But what we can do is be aware of our workload, routinely evaluate each thing’s value, and get a second opinion if ever there is doubt.