Letter 008 - Tactics for Running Kick-Ass Projects

Reflections on a failure I had + lessons learned from running a high number of complex projects successfully + a request for your tactics

Up-front ask: share your tactics! I’ll be publishing an updated letter with the ideas you’ve shared (and will be citing them too of course)

Letter 008:

I’m pretty transparent about failures I’ve had. I think it’s important to talk about failures, if only to let the people around you know that you aren’t expected to be perfect…that shit happens, and you try your hardest to learn and grow from the experiences.

Early in my career, after having kicked some serious ass on my first few projects (read: I was pompous and overconfident), I came across a project that I nearly ruined with my inability to manage it effectively. I failed. The words, “I can project manage” that I uttered rather arrogantly to a group of colleagues as I started the project haunted me for years. (I literally shuddered reading this #CringeAF).

Let me be clear about failure: it means I was removed from a project about two months early. “The error you made nearly ruined our credibility with the client” + “we need A players, and you’re far from that” + “we’ve brought in a more experienced consultant to take over your workstreams” == some of the things I was told (months after losing a very close family member, so not the best headspace to be in).

Everyone knew I was being removed. Everyone saw me walk out of our team room for the last time. Everyone knew when I went to our company happy hours. My next project knew. It felt absolutely awful, and the daily barrage of feedback (some delivered kindly, some rather brutal-bordering-on-cruel) I had received stuck with me. The experience destroyed my confidence and energy — it stuck with me emotionally for a long time. It took years of therapy + my own processing to come to truly come to terms with the failure (and, far more importantly, the family loss). But after that experience, I became a far stronger leader and eventually started garnering a reputation for running really fun, successful projects that beat expectations (it hasn’t all been smooth sailing, admittedly, but certainly better than the above setback I mentioned!).

As I spoke this week with one of my awesome colleagues around running kick-ass projects, I decided to write out some tactics for project kickassery (of course Urban Dictionary has a definition for this…). This person + you all have other tactics/approaches you deploy for project success, and I’d love to hear them in the comments or as a reply —> so that we can all get better together. I’ll likely publish an update of this later with whatever tips you provide (with credit given!)

For the new subscribers, a reminder that Exonomist is written quickly, in raw form, with minimal copy-editing, and the expectation that I’ll go back later and disagree with or refine what I’ve written previously.

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Running Kick-Ass Projects, A Memo

Dear Awesome Colleague,

So you’ve decided to take on a role leading a big initiative — congratulations! You were chosen because you have demonstrated abilities getting results, and people love working with you. As you go into this project, I thought I’d bullet-point out some tactics & considerations to keep top of mind. This journey is going to be challenging and fun. Expect moments of discomfort and frustration, along with feelings of growth and victory. Here are some tactics to help you maximize your project’s chance of growth and success.

• Start with Why this project has to happen and What it will entail. How does this effort propel the organization forward? Why does it need to happen right now? What exactly are you going to do during the project, and how will you know it’s successful?

  • Put your articulation of this onto a single page (word doc, slide, etc.) and share it with whoever is going to be sponsoring the project. Make sure you are 100% aligned. Do not try to speed through this step, walk the person line by line through this articulation, because misunderstanding here increases misunderstandings later. Oh, and did I say single page? Let me say it again: one page. The longer you drone on, the higher chance that people will get lost and miss your point

• Build momentum from the very first second of the project kick-off. I call this the “hot start” (been calling it that for years, not be confused with Andrew Chen’s The Cold Start Problem - great book btw). In this phase, you ensure that you’re ready to have an energizing kickoff meeting with every key stakeholder in the project. You need to be ready, in the right mental space to set the tone. Bring your authentic self, show your excitement, and remind people of the Why of the project.

  • Additionally, make sure you can have some wins on day 1 of the project, and that progress can be communicated on the exact same day. You want to set the tone that this team will move quickly. This can be as small as setting up your weekly meeting candence, getting a supporting meeting booked, setting up your digital workspace, etc.

• Make time for Ways of Working. I am convinced this is the single most underrated part of managing projects. If I had a dollar for every time a PM pulled me into a project, threw tasks over the table, told us the deadlines, and then asked when they could check-in, I’d have… a lot of dollars. What’s missing from this? The human angle, which is the most important part of managing projects. If a “project manager” doesn’t know the answers to the below questions, that person’s ability to manage in a harmonious, output-enhancing way is going to be seriously diminished… Take the time to make sure every key contributor on the team has answered the below questions.

  • How do you like to receive feedback?

  • What are your personal boundaries between work and your personal life?

  • What are your strengths?

  • What are your development areas? (what are you trying to get better at)

  • What do you do outside of work? Any hobbies? Fun facts?

  • What are your pet peeves?

  • How can we empower you to bring your best self to work every day?

  • Are you a morning bird or a night owl?

  • Do you need quiet time to process information, or do you prefer more active collaboration sessions?

  • etc. etc. (insert your ideas here)

• Define and setup your place of communication immediately. Wherever the team is going to stay coordinated, make sure those properties (apps, channels, files, etc.) are setup quickly. Make sure everyone has access. Consistently link back to these places of collaboration, and try to ensure that things like file structures are easy to navigate. Clearly label files so that they’re easily discoverable later. If you spend all this time creating artifacts, but no one can discover them and no one ever goes there, then your team will suffer from inefficiencies

• Run a Failure Prediction exercise. After the project has kicked off and you’ve gotten going with the team, send out a survey and/or do a group exercise where every single person answers the question, “What are the two most likely reasons this project could fail to achieve what we said it would on day 1?”

  • I use surveys when I’m in a low trust environment or in a massive project team

  • I ask this question in a live meeting when there is high trust and/or the team is small enough that everyone can share their opinion multiple time, with space to be a little verbose

  • In a 12-week long project, I’ll usually ask this around week 3 or 4. In a year-long project, around month 1 or 2 — whenever is long enough to have real performance data, but early enough that you can still get the project back on track

• Setup recurring meetings with other leaders on the project and make sure you adjust your cadence to keep you tightly aligned.

  • I’ve found that for the most important projects, we have to be meeting at least 2x per week

  • In highly complex, high-stakes environments, I'm a fan of the daily stand-up / collaboration meeting. This sucks when you don’t love who you’re working with…but when you do enjoy working with your colleagues, this is one way to leverage that relationship strength into raw fucking speed.

  • Additionally, don’t skimp on 1-1 meetings. Some things just will not be said in a group environment, and I find great joy and insight in the 1-1s with various folks on a given project.

• Have a list (I prefer this in slide format) of things like Key Dependencies to make sure that the team is tracking each dependency like a hawk, week over week. I recommend reviewing the dependencies you define as a team, going item by item and re-assessing if you’re doing enough to manage said dependency

• Have a strategic PM (read: not the same thing as PM) to help keep you on track and focused. Ideally this person and others are actively tracking RAIDS (risks, actions, issues, and decisions) so that there’s a log of key evolutions throughout a project.

  • I’d like to point out that PMs sometimes just do tracking of RAIDS, and that is totally fine, but your team needs for someone to be connecting RAIDS to Actions to be taken…and they need to be thinking about how to take action in a way that is harmonious.

• Track team morale actively. This usually takes the form of asking people in your 1-1s how you think the project is going, how it could be better, and how that person could be empowered to be even more impactful. “What is one thing that we should change to make this project more successful?” is one of my favorite go-to questions (usually people give more than one thing)

• Check-in regularly on both project tasks and team operations. While you’re doing your daily/weekly/bi-weekly status tracking exercise, take a step back to make sure you’re asking the entire team how things could be moving more smoothly. I love to ask this in a group setting as well as a 1-1 setting… In a 1-1 setting you get people thinking about “how could we be better?” and in a group setting, it’s their chance to share out their thinking + collaborate with others to potentially identify ways to quickly find a solution to test (…yet again helping people to see and feel momentum and improvement). Your team must become accustomed to continuously tuning how it operates, and you have to reinforce that every single person in the room plays a role, and that their voice matters.

• In one of the worst case scenarios, be prepared to make team member changes. Sometimes, the way a team was configured on day one just wasn’t the optimal configuration. There are many reasons why this could happen, but a quick reminder here: sometimes it just doesn’t work! I have absolutely had situations in the last few years where the person I was teaming up with was great, but we just did not mesh. Something was so fundamentally different about how we worked / communicated, that is was destined to not work. When this happens, be prepared to go into a process to either: (1) change scope of responsibilities to minimize conflict or (2) transition someone onto a different project (happened to me!). Ideally before this, you’ve attempted to do some mediation where you directly address challenges and try to work through them, but sometimes the effort to do this is both a distraction, and a potential risk to project success. There are kind, empathetic ways to make these changes. Don’t make them lightly, but don’t shy away from difficult conversations that are needed. This is the responsibility of a project leader — sometimes you have to make tough calls. It comes with the turf.

(insert eloquent ending to letter that my brain can’t come up with right now).

Hope you took one thing away from the letter here. See you next week!

MD