Ah startup life. It can be chaotic at the best of times, and for many of us, this is part of the appeal. Through no act of specific intention, we recently found ourselves in an unprecedented moment of multiple major initiatives having a “go-live” date all with in the same month. A series of delays, user feedback related pivots, some team restructuring, and a (un)-serendipitous confluence of schedules meant that we were to truly learn the meaning of “flat-out.” Unfortunately, we weren’t able to offset delivery dates and stagger the releases for various reasons, including satisfying the never end sense of urgency to strive for rocket ship type growth. In the end, we got there. We are a team of high performers, after all, but not without some easily avoidable stress and anxiety. Here are my take always from the experience.
Being overly busy getting things done is not an excuse for poor planning.
In our business where we are still relatively small, and it seems like there is always too much to do with too few hours in the day. Our managers have to be “do-ing” as much as or even more than on the time spent purely manging. In my case, at the “C-level” I am still in Canva whipping up ad content and writing copy for blog posts, and in order support the various campaign launches with fundamental deliverables, I struggled to step back and craft and maintain the detailed planning documents.
However, it is in these types of scenarios where this type of planning is even more crucial.
In the long run this resulted in various ad-hoc tools and templates thrown together to organise things, but these docs quickly devolve into messy Frankenstein spreadsheets that are difficult to follow for anyone not deep in the task. What is worse is when one doc gets too messy that a version 2 is created and suddenly we are working now across two sets of messy notes.
Understanding the right balance of project planning and governance with the agility that enables people to just to their job is a subtle skill. The right makeup of project management needs to be tailored to every project based not only on the size and complexity of the project, but also the individual needs the stakeholders, the team style and makeups and the overall company cultures. And while the PM style often times evolves as a project progresses, the exercise of establishing even the most basic of project management offices will ensure much greater success and smoother sailing after kick-off.
At the end of the day, project management is all about to-do lists. The art of good PM governance is in organising the hierarchy cascade from the broad down into detail. Key lists of goals are supported by itemised milestones and backlogs of sprint tickets. Artful planning is mindful of how the lists and sub-lists interact, demonstrate dependencies, provide input and feedback and ultimately connect the broad goals to the tactical tasks. This is not only about the functional organisational requirements, but also in service of the next major lesson I learned: visibility.
Clarity equals confidence
I may have it all mapped out and under control in my head and on the various aforementioned working documents, and we that are deep in delivery are 100% confident everything is on track, but for those on the outside, obscurity leads to anxiety. How’s it going shouldn’t be a question that needs to be asked directly when the right structures are in place to provide the visibility needed for my boss, the adjacent teams, and anyone else who may be peripherally involved.
People do not inherently trust that you are going to get it done, even if you have a good track record of delivery. People want to come along on the journey and be a part of the process, even is as just a bystander. They want to feel like they can provide input, even if you aren’t seeking it, or know they their input is not helpful. This is all part of working in an organisation, engaging others, responding to feedback, managing that feedback and moving forward with active buy in from those involved and those not involved.
The subtle skill of this component is in providing the right amount of info to the right people. Too much can invite the unwarranted, and sometimes unhelpful input or even scrutiny. Or course, I am not advocating for information siloing, but in the structure of the PMO, organising the various hierarchy of project progress according to the particular stakeholder needs can help corral the attention at the appropriate level of information access.
“Agile” shouldn’t abandon the fundamentals
Modern startup SaaS culture loves its set of buzzwords, and “agile” is certainly a favourite. I chuckle when I hear someone say “we are taking an agile approach” as a proclamation of the style of project delivery. When I hear this I wonder which parts of traditional project management will be neglected in the interest of lightening governance and oversight. Admittedly, my background in construction shapes my perspective, and when I discuss some of the principles of “waterfall” I get looks like I came up in another epoch. I always relate to my experience with building houses very much in the more linear approach of PM, utilising the seemingly archaic “waterfall” methodology. However, new ideas are generally built on the foundations of the past, and agile approaches still need to be mindful of the fundamentals.
Don’t assume that agile is necessarily faster, easier or more simple
Communication updates and clear project progress are more difficult to get right
There are still clear milestones to achieve