How to Get the Most Out of
Your Execs
Read on my website / Read time: 5 minutes
This is for the pro product folks out there...
Would you believe that out of all the folks who have reported to me across all the companies I've worked at in the last 24 years, only 6 of them sent me consistent updates?
Sounds crazy, right?
From VPs to Directors to individual contributor product managers.
Sure, since they reported to me, I would follow up with them and we had our regular 1:1s and team meetings.
But it often required me reaching out to them vs. them proactively informing me.
Which only made it harder for me to be able to support them in their time of need.
To be fair, though, this really comes as no surprise.
Most product managers fail when it comes to keeping their bosses and executive stakeholders in the loop.
Why?
There are a bunch of reasons. Product Managers are incredibly busy people. You have no time and it's understandable if you're like, "Now I also gotta write this email update?"
You don't want to look stupid either. Maybe things aren't going as good as they should be. It's natural to not want to share that. It's natural to think, "I'm going to fix this and then I'll send an update." It's natural to only want to share good news.
And you don't want to waste your boss's or an exec's time by sending the wrong info.
I get it.
But in my experience the biggest reasons are (1) they don't realize the importance of proactively communicating "up", and (2) they don’t know what to include, or even how often to communicate.
So, today I'm going to talk about the importance of sending executive updates and how to do them. Plus, two pro tips to make you really look like a rock star.
I'm going to share what I've done in a lot of companies and examples of what I've seen others do, both in product roles and outside, who are really good at keeping senior execs informed.
Why senior exec updates are important
You've been hired to help manage and grow a multi-million dollar product. An investment decision was made and budget was allocated. And that includes your salary. Management has trusted you to do a job. It's important you keep them informed.
- Provides them with crucial information, enabling them to make timely and informed decisions - essential for you to help keep your product plans on track.
- Allows you and your exec stakeholders to regularly ensure there's top-to-bottom alignment with the most important priorities.
- Builds trust by providing transparency into your and your team's activities and demonstrating your self-accountability.
- Enables you to flag potential challenges or roadblocks before they escalate into major problems, allowing for proactive solutions.
- Gives you visibility - which will become important at performance review time and when you're up for promotion.
So you want to send them something - if for nothing else other than for visibility.
3 aspects of sending exec updates
Depending on the size of your organization and the nature of your role, you may have different levels of executive audiences to cater to.
The best way is to be consistent and include the right information for the right audience at the right time. Doing this will keep your exec stakeholders invested in you and your success long after you've been assigned to the project.
Frequency:
Your boss: Weekly.
If you're in a smaller organization, like a 100-500 person startup, you likely have direct access to the senior executives (e.g., you're in a product role that reports to a C-level/SVP/EVP) or you're a skip level or two away (you report to someone who reports to the C-level). In this situation, I would recommend more frequent updates - and it may even be required. Minimally, biweekly. Sometimes, even weekly may be required.
If you're in a larger organization in a product leadership role, generally you want to provide an update every 2 weeks, if not weekly. If you're in an individual contributor role, align with your product leader on the right frequency, but generally I would recommend not going more than a month / 4 weeks.
If you're in a super large organization, there may be a formal reporting structure to follow. At an individual contributor level, I'd recommend every 2-4 weeks for your key executive / management stakeholders, and monthly to quarterly for senior executives above that. At a manager / leader level, I'd recommend more frequent updates in between those timelines that synthesizes key updates from across your team.
In any of these cases, always keep your boss informed more frequently and PRIOR to the broader update. You want to keep surprises to your boss to an absolute minimum.
Format:
- Open with a headline to anchor the update. For example, the overall state of the project ("We're on track", "There's some risk with contingencies in place", "The project is at risk"), quickly followed by something quantitative ("We're 2 weeks ahead of schedule", "The project is at risk and behind by 2 weeks", "We're 20% off our goal this quarter") to put the headline in context.
- If you're reporting numbers, get to them ASAP.
- Start with any bad news first. End with good news.
- Share 1-2 key highlights, if appropriate. E.g., we just hit a big milestone, shipped something major, solved a huge problem, received kudos from a customer, etc.
- 1-2 of the biggest risks that they need to know about - e.g., running over budget, deadline risk, major dependency risk, resource constraint, etc.
- Also, if applicable, I like to highlight a team member whose work has been especially great lately.
- Keep it concise! Use bullet points as much as possible.
Call-to-Action:
Include an ask. I see so many product managers and even product leaders not take advantage of this.
I get it. Asking for help can feel like we're failing. That we'll be seen as not fully competent. You don't need to be a superhero.
Asking for help isn't a sign of weakness. It's a sign of competency.
On the other hand, I've worked with product managers and product leaders who didn't even know they could do this!
Your executive stakeholders - and especially sponsors - are supposed to be there to support and help you. Because, believe me, when you've hired someone to do a job, it's because you believe in them and you want them to be successful - because their success is your success. (Especially your boss!) They've invested in you and they want a return generated from their investment in you. They WANT a huge outcome. So, let them feel invested and INTEGRAL to your success. Put them to work!
Of course, you don't need to make up an ask just for the sake of it. And you certainly don't want to ask them to do work that's expected of you and your team.
Here are some asks I've made of my sponsors in my updates:
- Resource asks.
- Unblocking resources.
- Clearing conflicting priorities.
- Timely contract approvals. ("The vendor contract has been delayed in Legal and we need help getting it approved in order to hit our next deadline.")
- Scope vs. time vs. budget trade-offs.
- Spending approvals.
- Other critical trade-off decisions.
Examples
There are many templates out there in the wild that you can use. Here I'll share some real-world exec updates you wouldn't normally think of. (Confidential info redacted/replaced.)
Example 1:
Project X is on track. We’ve delivered over 53% of our in-scope features, and we’re on track to launch publicly in May.
A key highlight was completing of the Z Feature, which we recently demo'd to Customer Y. Their CFO said: "This is game changing and will revolutionize the way we do Workflow W!"
I also want to particularly highlight V’s design work - she's been able to turn around design updates very quickly and every time we share a new demo with our user research group they rave over how much they love the design.
There is some cost risk. In order to make the deadline, we've had to take some short cuts in our code build that will require us to increase our Google Cloud spend by 25% when we put this into production. We either need to decide that cost is acceptable or add some extra time to the project schedule for performance optimization. I need some guidance from this team on this point: Are we ok with this cost in order to meet our timeline?
Thanks, any questions?
Example 2:
We wanted to provide an overall update on Product App. This is me being the messenger for a lot of work by the collective team (the credit is theirs).
UPDATE:
DEVELOPMENT
- Graphics for how app is hosted and invoked are in the works and targeted to be shareable with you next week
- Mockups of App using available Third Party APIs are also in the works and targeted to be shareable with you next week. We are working to get Engineering's perspective on LOE and feasibility.
- J is working on thoughts on the API that could be externally shareable using some of the research that we did on what others are offering. Full disclosure though there is a lot on their plate.
- Vendor X conversation is setup for next week. Key focus will be how we would make this tangible after the announcement at our User Forum (e.g., organizations in their client book that could be initial targets).
OVERALL
- Partner Y opportunity going well but still early days. We met with them this week to walk through a proposed scope, and it was well received. As we have supporting materials available (e.g., standards, technical information, business considerations), we are and will be sharing these with them. They are very interested in a partnership with us (D, their CXO, reached out to you), but still unclear how much interest there will be around a joint app. B is the assigned Product Manager and C is leading the business relationship. <link to deck>
- Overall app process design is in a solid place. Below is a link to where we've captured the high-level process including partner and our activities and supporting documents. We are using a modified version of this with Partner Y. <link to deck>
- The first two key documents in the workflow process (Doc 1 link, Doc 2 link) are ~75% complete and soon to be ready to share with early clients interested in the app. Until we have the fleshed out the API later in the year, the process assigns Y and Z resources to help scope the work needed on both sides. <links to docs>
BUSINESS / STRATEGY
- Contract template is in the works due to some hard work by A and C. Looks like we will have an 80% version of this by the end of next week.
- Goal is to finish 1st version of financial model by Wednesday of next week. This will help us make strategic decisions on pricing and needed resources to continue to support the effort holistically.
Thanks,
<name>
Example 3:
Susan,
I hope your week is wrapping up well. I wanted to follow up on the effort to get Project Olympus scoped, estimated, and tracked with a timeline. We made some significant progress as called out below but do not have an operational timeline yet. This is due to still working to get the team spun up while not impacting other key Q2 deliverables. It looks like we could have some key members of the team spun up next week and potentially be able to estimate and timeline the effort then.
PROGRESS
- Developed high-level requirements document (<link>) and reviewed and refined with Chris and Xi.
- Met with Barry to prep initiative tracking report.
- Updated playbook with key visualizations - Carlos <link>.
- Developed sandbox and working patient identity call - Sameer.
NEXT STEPS (Owner)
- Review scope with you, working to get time with you next week (Charlie)
- Refine scope based on discussion with Chris and Xi, e.g., user consent considerations (Carlos / Charlie)
- Estimate LOE for the scope which includes getting the tickets put into JIRA (Carlos / Charlie)
- Develop timeline and tracker for initiative (Barry)
- Review LOE and resulting timeline with you for feedback (Charlie)
- Continue building out tools for app effort (Xi)
FYI: we've pulled in Fernando from Kathy's team to help lead the PM effort around the Atlas, Apollo, and Zeus initiatives.
Thanks,
Charlie
Pro tips:
Don't go silent. I get it - you're trying to get stuff done, meet some deadline, maybe things are a bit in flux right now, maybe something's gone wrong, maybe there's not a lot of new information. The default state is to want things to settle, be confirmed, be fixed, or be new, and then send an update. Wait for the win and then send the update.
DON'T. Send something on a regular cadence. Even if it's, "everything's on track."
When I did sent regular updates, sometimes in the beginning I didn't get too many responses, but once I established a regular pattern, I learned my updates were something folks not only expected but actually looked forward to. And it quickly established me as a leader and someone who could be seen as reliable and accountable.
Send the same update to your team. Your team knows what's going on anyway. So if they see the way you're communicating to executive stakeholders, and they see the priorities and goals you're setting, they will respect that you've made that commitment, and they're more likely going to support you and give their all. It creates an amazing sense of collaboration and transparency within the team.
Summary
The cool part is by using this approach your executive stakeholders will love you and find new and unexpected ways to help you out.
I've worked with CPOs, COOs, CFOs, founder/CEOs, and other executives who ALWAYS replied to my updates.
They were all incredibly busy people, but they still took the time to read my updates and send a response. They always asked great questions or provided meaningful insights that propelled me into new and exciting directions. Sometimes they'd just reply with a quick, "Great progress, thank you" or "Thanks for the update", which was still awesome.
Being consistent in your executive updates is the best way to ensure you’ll have their support as you grow. And remember, if you’re struggling, going silent only makes it worse.
Your Action Item
What's your #1 takeaway from this? What aspect of sending updates did you not think about until you read this post? Will this change how you do your exec updates or how you develop your relationships with your executive stakeholders?
