The "Dark Arts" of Stakeholder management

November 2021, updated January, February + March 2022, January + April + August 2023

What do successful collaborations (with stakeholders, colleagues, mentors, managers, etc.) look like? Great question! They're partnerships, where each party trusts the other(s) that they're doing good work (and work with them to get there if they're objectively not) -- and helps each other be successful. 

This is easier than it sounds! As an advisor, mentor, educator and advisory board member, I've collaborated with 100s of stakeholders. Here's my advice on how to help you get there -- to build trust and rapport with your current -- or next collaboration, whether you're managing up, sideways or across.

If a collaboration goes south, depending on the circumstances, it may negatively affect your collaborators, colleagues and even the company's bottom line, which in turn can affect your performance evaluation. Here's how to try to avoid this: by aiming to get on the same page with your collaborators as much as possible -- so that there are no surprises, for anyone.

Statement of the Problem

One thing that's always rang true for me, in my career in Data (and developing data products):

The biggest pain point when it comes to developing data products is -- not data! -- but cross-team alignment, whether that’s around communication styles, priorities, deadlines, deliverables, something else, or all of the above. 

In my blog post on "How to Deliver Business Impact with Data", I shared my strategy for successful kick-off calls with prospective (internal or external) collaborators, where at the end of the call you’re on the same page and know where to go next. The blog ends with recommendations on next steps, including having check-ins in place. 

Now that you’ve landed that coveted data product -- or client -- what can you do to make sure the collaboration (and check-ins) are a success? Or, if the kick-off call -- or check-in -- didn’t go as expected, what can you do better next time?

Here's my advice, based on my many collaborations, for how to get on the same page with someone in a way that also builds trust and rapport.

"Meeting" Definition: As an aside, with more and more companies going remote, I'll loosely use the term "meeting" to mean a way to connect; it need not be in-person or over Zoom, and includes async communication in Google/Notion docs, Slack check-ins, etc.

What do you need to be on the same page about?

Having collaborated with many stakeholders over the years, the #1 thing that I’ve found that works for me, to get myself and my collaborators (back) on the same page throughout the data product development lifecycle -- is to understand, both:

From "How to Deliver Business Impact with Data", this includes: 

What we also need to be on the same page about (with more advice on how to do so below):

The goal is to not surprise/blindsight the stakeholder on the day that the (intermediate/final) deliverable is due. 

How do you know if you're on the same page?

I don't propose an engagement, but share advice on things they can try instead.

How do you actually try to get on the same page? What do those iterations look like in practice?

Challenge 1: Stakeholder Wants to Meet More Often

Symptom: Stakeholder is not on the same page about the direction and progress of work. 

Solution 1: Check to make sure you're providing all of the needed context around the direction and progress of the work. That is, does your (sample, async/sync) update include:

And that as soon as blocker B happens, let your stakeholder know about it, along with what you'll be trying next to either:

What you don't want to happen is, if you change direction on B when your stakeholder was not aware and took next steps in their work assuming B will be done -- when that's no longer the case -- you'll (inadvertently) blind-sight or surprise your stakeholder(s) -- on the day of the deadline -- that you won't be delivering on the original ask, because the project went in a different direction or because you've been blocked for awhile. You'll immediately lose rapport.

Please note: This approach/solution is a good first start for check-ins, but do get feedback from your stakeholder to make sure that the updates are really tailored to their needs, which be to stay informed r align on next steps, or something else entirely, or all of the above.

Solution 2  (AKA Iteration 1): (Especially if Solution 1 is not working)  Just ask! I tend to frame it as "Are you able to share more context about the request? Are you looking for more frequent updates?"

Solution 3  (AKA Alternative Iteration 1): (Better yet) If you're feeling you're not on the same page with the stakeholder, proactively reach out! I tend to frame it as:

Challenge 2: Stakeholder not Replying to Questions

Symptom: Not understanding the communication style of your collaborator -- and you're reaching out in a way that either is not resonating with them -- or it's not the most convenient for them.

Solution 1: I highly recommend asking about their communication style and preferences during the intake/kick-off call. It’s a question rarely asked but is so important for the collaboration that it builds almost instant rapport.

If you forgot to ask, watch for:

Solution 2 (AKA Iteration 1): You forgot to ask the questions shared on Solution 1, but have an idea on what their style and preferences are. Reach out (in your stakeholder's preferred style) to confirm. You can frame it as "it will help us collaborate better" -- which it will.

Solution 3 (AKA Alternative Iteration 1): Just ask! You can still frame it as "it will help us collaborate better" or "it will help me get you an actionable result faster" -- which it will.

Challenge 3: Business Question or Impact not Clear -- or the Request is "Everything"

Symptom: You think that it may take many weeks or even months to get an answer, and/or may include your applying the state-of-the-art ML to be able to begin answering the question for the first time, or -- it's not even clear what you are trying to achieve and why, expectations are misaligned. 

Solution: To get on the same page, I highly recommend asking questions (which I share here) during the intake/kick-off call to get on the same page about all aspects of the data product, including deadlines. 

If you forgot to ask -- or realized you had more questions, if you understand how your stakeholder prefers to communicate (and if not, see advice in "Challenge 2"), reach out in their preferred style (and format), to share what you think the business question is, and the scope of work to help iterate -- and ask if you’re on the same page.

If it turns out you're still not on the same page, ask follow-up questions. I tend to frame it as: "We're trying to get to X (where X is the highest-priority business initiative for that quarter). When in the past, I've had experience getting to X, I did it via A, C and D. To get started, we'll focus on customer activity in the last week. Does that sound like a good first step? If not, are you able to share more context?"

Challenge 4: Losing Sight of End Goal

Solution: If you know you have high attention to detail (like I do), to make sure we get back to the "big picture", it helps to:

Challenge 5: Deliverable Doesn't get Used -- or Doesn't get Used as Expected

This is super frustrating! You've put in a lot of work. If the deliverable doesn't get used -- or doesn't get used as expected, you might have a "Challenge 4: Lost sight of the End Goal" or "Challenge 3: Business Questions was not Clear".

Solution 1: Let's take a step back and re-assess:

Then following advice in "Challenge 3", discuss your ideas for next steps on how to make the deliverable actionable.

Solution 2 (AKA Iteration 1): Just ask! You can still frame it as "I saw that we ended up not using the work

Challenge 6: Stakeholder Wants you to Read their Mind

Symptom: You don't have all the information you need to decide on next steps. Depending on the stakeholder, you get the feeling that the stakeholder is too busy to reply (try advice in Challenge #2) -- or requests for more context are not welcomed. 

If it's the latter, Solution 1: Let's take a step back and re-assess:

Then try the advice in "Challenge 3: Business Questions was not Clear", reach out to your stakeholder, outlining:

If you don't know what these can be, make an educated recommendation -- and ask them to confirm that you're on the same page. Framing this request as check-in to make sure that you're on the same page -- will help you get there, and will also build rapport. Chances are, you'll get: a "yes" back, more context, or a request for a meeting to discuss the plan further. All wins!

Challenge 7: Stakeholder is Surprised about the Direction the Project went in

Symptom: You get asked, why did you end up doing X and not Y? Or why did you do project X and not project Y first?

Solution: try the advice in "Challenge 1: Stakeholder Wants to Meet More Often", because you're not on the same page about direction or next steps for the project, or what the priorities are among the projects you're juggling.

Challenge 8: Stakeholder has a "Quick Question" or asks "Why are Things Taking so Long"

Symptom: You're not on the same page about scope, challenges/blockers, or trade-offs around complexity, risk, accuracy or what the final deliverable should look like.

Solution: Is there a way to visually illustrate where the complexity in the project is, so that it's easier to get on the same page?

This is especially true if this is the first time you're using a data source , and especially true if it's the first time trying to use multiple data sources for the first time -- and don't  know what's there or not, or what the quality is, or even you'll be able to join them together.

This is especially true if this is the first time you're trying to answer this question (by creating a metric or a baseline) -- or if there are other higher priorities. Does your stakeholder know about this? How have they handled similar questions in the past about this?

And also outlining the points shared in advice in "Challenge 6: Stakeholder Wants you to Read Their Mind". This way, you'll be on the same page if, for example, the deliverable is a POC, or if the scope has been expanded to production-level, and you need to propose phases and iterations of deliverables for this collaboration.

Challenge 9: You've been Committed to Something you Didn't Know About -- it Kicked-off Yesterday (!) -- and you Don't have the Bandwidth (!!)

Anyone that's ever been my direct report has learned that I don't (and don't like to) assign tasks/projects to people -- because if I do, this exact thing may inadvertently happen.

Symptom: You're not on the same page about what else is on your plate, but you already knew that. 

Solution: Connect with your stakeholder to let them know that "you've been committed to something you didn't know about, it kicked-off yesterday, and you're just finding out about it. What happened?" And let them talk. 

Depending on your availability, you may consider proposing a collaboration on a scoped down version of the data product for a proof-of-concept as a first step, which will help you -- and anyone else -- contribute to the data product.

Alternative Solution: Loop-in your manager. Are you, your stakeholder, and your manager on the same page about priorities? If not, consider suggesting that your manager sync with your stakeholder first, then you can collaborate on the plan (mentioned in Solution 1 above).

Parting Advice

You can do this! Don’t forget, the goal is to get everyone on the same page, every time! If it helps, it's always an area everyone can improve. :)

I know I’m on the same page with my collaborator when they can finish my sentence (!) about what the next step is. This way, it’s easier to develop data products, make/save the company lots of $$$, and be more visible. As a side effect, your resume or portfolio will have more actionable bullets. Good luck! 


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