Tent Talks Featuring Helen Keighron: Keeping the Team Together: Lessons in Leadership and Alignment

Tent Talks Featuring: Helen Keighron
Helen Keighron
Fractional Design Executive
Helen Keighron is a fractional design executive and startup advisor focused on helping SaaS companies of all sizes unlock the business value of design and avoid common scaling pitfalls.

Join us for a thought-provoking Tent Talks session with Helen Keighron, a seasoned design executive and startup advisor, as she explores the concept of “alignment” within teams and organizations. Drawing from her extensive experience in scaling teams and enhancing user experience, Helen will discuss the nuances of creating and maintaining alignment—beyond mere consensus—emphasizing the pivotal role of communication and leadership in steering teams towards shared goals.

This session will equip attendees with practical insights and strategies to foster a cohesive team environment, manage diverse viewpoints, and drive effective execution in their own organizations. Prepare to engage with Helen’s expertise in a lively discussion that promises to demystify alignment and inspire leaders at all levels.

Session Notes

Session Overview

In this Tent Talks session, Helen Keighron, a seasoned leader, shared her expertise on keeping teams aligned and focused through effective leadership. The discussion explored the importance of defining alignment, understanding strategic priorities, and overcoming common pitfalls that leaders face. Helen emphasized the necessity of clear communication, psychological safety, and shared understanding within teams to achieve alignment. She provided practical strategies for simplifying complex messages and maintaining focus as projects evolve. Helen also shared personal experiences and insights on navigating challenging alignment issues in high-stakes environments.

Helen highlighted the importance of flexibility in execution, the role of psychological safety in fostering open dialogue, and the need for leaders to create environments where diverse viewpoints are encouraged. She also stressed the significance of clear and repetitive messaging, the value of written communication plans, and the need for leaders to constantly engage with their teams to identify and address misalignment. By sharing her experiences and strategies, Helen provided valuable insights for leaders looking to keep their teams cohesive and aligned in dynamic and complex project environments.

Common pitfalls leaders face when creating alignment:

  • Definition of alignment: Varies among individuals based on their experiences.
  • Strategic understanding: Importance of knowing why a task is strategically important.
  • Role clarity: Everyone should understand their contribution to the desired outcomes.
  • Key barriers: Misalignment in vision and strategy, shaky planning, misaligned incentives, and emotional challenges in decision-making.

Balancing diverse viewpoints and common goals:

  • Shared understanding: Ensuring everyone understands the outcomes and actions agreed upon.
  • Healthy discourse: Encouraging evidence-based discussions without fear of social pressure.
  • Psychological safety: Creating a safe environment for proposing ideas and viewpoints.
  • Learning culture: Emphasizing learning from failures and supporting open communication.

Simplifying complex messages:

  • Repetition: Necessary for messages to sink in, especially in larger organizations.
  • Cartoon clarity: Boiling messages down to simple, clear points that can be quickly understood.
  • Multi-channel communication: Using various mediums to reinforce messages.
  • Written comms plan: Ensuring clarity and thoroughness in messaging through written plans.

Achieving alignment in challenging situations:

  • Case study: Building a new product with high technical and regulatory complexity.
  • Design sprint: Using system maps and OOUX activities to align teams on a shared model.
  • Rapid testing: Iterative testing with customers to refine and validate plans.
  • Micro shareouts: Regular updates to keep stakeholders informed and involved.

Signs of losing alignment and steps to realign:

  • Indicators: Vague reporting, stalled progress, tensions, and finger-pointing.
  • Diagnostics: Speaking with ICs, maintaining cross-functional relationships, and understanding different perspectives.
  • Timeline creation: Tracking changes and decisions to identify points of misalignment.
  • Role clarity: Using frameworks like DACI for decision-making and accountability.
  • Celebration and recognition: Acknowledging achievements to boost morale and reinforce positive culture.

Notable Quotes

  • “Healthy alignment means you’ve built a shared understanding of the problem to be solved and people know the desired outcomes.”
  • “Teams should have flexibility on how to achieve outcomes, rather than being given prescriptive plans.”
  • “Psychological safety is crucial for healthy dialogue and team identity.”
  • “Leaders owe teams clarity on decision-making processes and expectations.”
  • “A lot of companies will say something like it is our strategy to increase sales by 40 percent, and that is a goal that is a desired outcome, but it is not exactly a strategy.”
  • “Alignment does not mean that everyone does something the same way.”
  • “It’s okay to have an idea that turns out to fail or to be wrong as long as you learn from it.”
  • “You can always tell comms went well if you get back, ‘Okay, cool. That makes sense.'”
  • “Help your team understand how to bring rationale and really help people see what you see.”
  • “At the end of the day, alignment health comes down to strategic clarity.”

Reference Materials

  • Books:
    • “Good Strategy, Bad Strategy” by Richard Rumelt
    • “Turning People Into Teams” by David and Mary Sherwin
  • Podcasts:
    • Amy Edmondson’s podcast on psychological safety (Harvard Business Review)
  • Articles:
    • Christine Perfetti’s Tent Talks episode on strategic rallying

Session Transcript

[00:00:33] Chicago Camps: What are some common pitfalls leaders face when trying to create alignment and how can they avoid or overcome these challenges?

[00:00:41] Helen Keighron: That is a great question. I think the first thing that’s important is to actually define what alignment means because people do have different conceptions of that. And we all come with our own lived experience to any process at work.

Theoretically, there’s going to be some set of activities that a team is going to undertake that are going to get them to a conclusion and a plan for next steps. And for me, like that means there’s alignment happening at multiple stages in that process. So it’s not like a one time activity, but the definition that I really like when you’re in healthy alignment, it means you’ve built a shared understanding of the problem to be solved and people know the desired outcomes of any solutions that might be on board.

The second piece is really understanding why does it make strategic sense to spend your time here? Teams have. Limited time and there’s always resources that are in question. So why spend it on this versus other things that they could be spending their time on? Can people relate the logic behind decisions that are taken about where to focus or about how to approach their problems like back to their teams?

And this is especially important, if you’re a middle manager and you might have layers of an organization to work through and you’ve got to bring that messaging along really clearly. to the folks who are, actually doing the work. And then finally, everyone needs to understand what is your role in really upholding these decisions that have been taken and producing the desired outcomes.

And this applies to everyone up and down a chain, no matter how senior you are. Even if you’re an IC, you still should be able to look at, this is the scope in front of me, and here’s how I know that my activities will contribute to the positive outcome that the organization is aligned on. In terms of the barriers to getting there, there’s really four big ones.

So the first one is something is off with the vision and strategy. And we all know that never happens. It couldn’t be that. Organizational and planning muscles are a little bit shaky. Potentially incentives might not be syncing up potentially within cross functional teams or potentially even cross departmental, like maybe marketing and sales are not aligned with product.

And then there’s also the last aspect is just managing the emotions that come into play around decision making. Some people are just afraid to make a decision, they lean into consensus too much, and that can have a whole series of knock on effects. I’ll talk about the the first point, and I think there’s two major branches that you can start exploring, like this is your chance to put on your detective Pikachu hat and start really digging in.

The first point is, do people not understand what has been communicated to them? And then the second branch is, do they not agree what has been communicated to them? And so those are two completely different things. And so you need to start having conversations up and down the line and try to figure out like where is that disconnect.

So you can pull out all of your communication at work superpowers and start exploring. Without bringing your own opinion to the question, without bringing judgment to the questions. For one example, if you said, hey, I think this strategy is silly. What do you think? That’s probably going to get you a very different set of answers than saying, how clearly do you see what actions your team needs to take to support our 2024 strategy?

Or how would you explain our strategy to someone new who’s joining the team? And you’re probably going to have to take the results of those conversations and then really play that back to your partners and potentially upward. And so you want really strong evidence as to where the disconnect might be so that you can fix it.

If the problem is that the message is misunderstanding and then you can look at do teams have enough background context, do they understand the mechanics of the business? Maybe there’s a refresher needed on some of the strategic KPIs that the business cares about and how that actually connects to their work.

Maybe they actually agree with what’s being said. They said the message sounds good, but then they’re having trouble, really translating it down to the thing that they own. And that’s something where you can step in and really help them break that down into smaller parts and make some of those connections.

As leaders, we have to do a better job of connecting the dots and just really ensuring that the strategy gets expressed throughout the planning mechanism. And that happens in different ways in different organizations. Some places might use OKRs. Some places might use a goal setting process. You need some sort of unifying thread that helps people get down to the team level.

If the messaging is just confusing, then maybe there’s a simpler way to say things. So this might be where some storytelling and some applied examples can really help. There might just need to be some more communication on this topic, and it takes a lot of repetition to do that. If the problem is people disagree, so ideally you can encourage everyone to have a healthy discourse about this and really bring their evidence based POVs.

I don’t like it is not necessarily an informed perspective. And disagree and commit is a valid option for moving forward here, but sometimes you have to help your team really understand what does that mean for them and why you’re still on board with supporting interaction, even if there’s other options that your team might like better, but you have.

Disagreed and committed as a leader and sometimes to the problem can be what leaders say is a strategy is not actually a strategy. So reading good strategy, bad strategy by Richard Rommel really helped me clarify this a few years ago because a lot of companies will say something like it is our strategy to increase sales by 40 percent and that is a goal that is a desired outcome, but it is not.

Exactly a strategy. It doesn’t describe the customer pain to be solved for. And it doesn’t describe how the plan for your company’s approach will be different from a competitor’s approach. So I think that’s really important to get clear on that. And you see this all the time, even some of the strongest companies in the world take this reductive approach.

And I think there’s a couple of things that you can do here. One is, if you feel like people are shaky on the underlying customer problem and how that impacts the business, Christine Perfetti, I know, did an episode of Tent Talks a few weeks back and I love her strategic rallying approach and I would really encourage people to check that out.

I’ve sat in a room with her when she’s done that with a company that I’ve worked for and it’s just amazing how quickly that process can ground stakeholders. And In those customer problems and the business needs and then come out with just a much more robust approach that you can actually turn into something that approximates a strategy or potentially you can’t pull that off that and getting everybody into the room.

But what you can do is put some back pressure on a weaker strategy through asking clarifying questions and maybe something’s been handed down, but what you can do is try to interrogate your understanding of what’s being said and coming up with the best ways to measure the outcomes to ensure that your team is accountable.

That is usually not like a very threatening approach. Everybody wants good outcomes. Everyone loves the concept of accountability. State your assumptions and that kind of draws stakeholders into a conversation. So if you’re saying, Hey, we believe by creating this new set of functionality, then users are going to start to take these types of actions.

Then we can measure those as leading indicators. Does that sound good to you? Because we think that, when we see more of these behaviors and we think that the output downstream will be this other thing that you care about. And so we can measure all along the line and make sure we’re on the right track.

And hopefully leaders can weigh in and they can say, does that connect to the outcomes that they were hoping for? And if nothing else, then you have got some air cover for the team in terms of what you are being held accountable for. So the next piece around the planning muscle, so maybe the vision and strategy is perfectly clear, which is great.

But the team doesn’t have a good planning muscle, so maybe the execution piece feels like it’s all over the place in terms of who makes decisions and who does what. So it can be a real pitfall when leadership starts making really prescriptive plans as a way to try to get people aligned. And it sounds logical, make a plan and people will stick to it.

But what ends up happening is teams feel really disempowered. So as a leader, you’re going to really want to think about setting standards over a process. So share your guardrails, share the outcomes that you’re looking for. And teams have more context than you. So you need to leave flexibility on how people get to the outcomes.

Alignment definitely does not mean that everyone does something the same way. And ultimately the plans for execution really need to come from the team to be strong plans. And so one thing that can work better to get to stronger plans, and this is a process a number of companies use, including Airbnb, I’ve heard we used a version of this at HubSpot, but it’s called a W-Shaped framework.

So essentially, if you picture a sort of drawing on a W, the first slant down as leaders are sharing some context downwards, leaders have to align first amongst themselves before they can share that context to make sure everybody’s hearing the same message in the same voice. But then teams process that and they’ve got their own plans they’ve been thinking about, and then they share those plans back upwards.

And then the leaders can look at the proposals from the team and integrate that thinking into their own, and then really start sharing here’s a good use of framework for how this half or this year is going to shape up based on where they want to invest and how they’re responding to the team’s plans.

And then teams make tweaks and send a final version back up for confirming buy in and getting us off to the races. And so another pitfall, mixed incentives. We are constantly balancing feasibility, desirability, and viability as a team. Sometimes starting with functional interest versus focusing on the core problem to be solved can really get you in trouble.

So you may have some things that you want to do to, let’s say, drive forward improving the design system, but you have to understand the bigger picture of how this work fits in and really help your partner see how focusing some time on that would improve another outcome that the team is accountable for.

Different functions are responsible for different aspects of a project, and ultimately ideally, everyone’s putting their skills together, and they’re trying to move those input metrics, and then lagging indicators that they are going to be held accountable for. At worst, though, some teams may be held accountable to completely different key results, and that’s where a system like OKRs, which is Objective and Key Results, Or even just a list of goals and play as a ladder up to those goals can really help de conflict this.

So you can see, okay, here’s the top level company priorities. And then here’s how all the departments across the company are thinking about those and ingesting them. And so you can pretty clearly see, okay, so product wants to do this thing over here, but marketing has a completely different idea. People should talk.

And it’s a nice way to catch that as soon as you can. On the last point, so mistaking alignment and consensus, now, if planning and decision making, if you find it’s churning along, then you are very likely wasting cycles on just the perceived security of what it will feel like when everyone agrees. And the thought is super well intentioned, theoretically, like everyone agrees, everyone’s going to feel good, they’re going to be invested, things are going to happen, and that’s not usually true, unfortunately.

So you’ll end up with a ton of compromise, very likely a pretty watered down set of commitments. So to actually get to a stronger agreement versus a consensus, there’s definitely some tactics that you can deploy. One I’ve seen used to really great effect. It’s when everyone gives input anonymously, such as forced ranking without seeing the results that other people are entering, and then leadership takes that into consideration.

We would do that at HubSpot as part of the product leadership team to get aligned so that we could give coherent guidance to teams in the first place, that first part of that W framework, and then get them responding. And then once teams submitted their plans, we would align again to come back with, Hey, here’s the final kind of framework for investment that we’re thinking about.

And it’s also really important that there is a single threaded owner for decisions. That person might be the most senior person, like your chief product officer. It might be somebody who is delegated by another member of the executive team, like a VP of product or VP of engineering. And that person must be in the position of making a decision that isn’t universally popular, but they can still be transparent on what input did they consider?

And then why did they make the decision that they did? That transparency and that follow up with the teams is really important. Those are my best tips on tackling some of those carry pitfalls, let’s say.

[00:12:01] Chicago Camps: You’ve pointed out that alignment doesn’t necessarily mean consensus. How do you maintain a balance between encouraging diverse viewpoints and ensuring the team remains focused on common goals?

[00:12:12] Helen Keighron: A good reframe is that we’re looking for everyone to have a shared understanding of the agreements that have been made. These agreements describe the outcomes that we’re looking for and the actions that everyone is committed to. We talked a little bit about what some of those methods we could use to get some of those points of view heard might be.

Things like the W-Shaped planning framework or having teams submit anonymized input. And unfortunately we’ve seen when things go tragically wrong, when everyone in an organization just gets along to get along, and they don’t submit their insights for consideration. When you do a postmortem on something that didn’t go well very often you will find times when someone withheld some information.

Usually due to feeling like it was, some kind of social pressure or fear or even thinking like, everyone must know this. I don’t know if I need to say it because they’re not concerned, which is actually called pluralistic ignorance. That’s a term I learned recently, and I will take that to heart, but the extremes are examples where, let’s say like the Boeing 737 MAX development quarters got cut.

And it was like the internal joke about like how terribly everything was going and no one spoke up. No one did anything about it. And there’s like disastrous consequences, like truly devastating consequences to that. This can compound, like depending on the types of problems that your team is solving. So you might be in some kind of murky waters with a big trust and safety issue or some ethical implications, or maybe you are working on something like medical devices or something that is really important to get any concerns logged and heard.

Obviously the foundation for healthy dialogue comes down to team identity and psychological safety. Leaders have to create an environment where there’s room in the process to propose ideas and express alternative points of view without fear of being persecuted for sharing a different perspective.

In reality, like there’s multiple ways to get to most outcomes and it’s really fair to evaluate everyone. Some are going to be maybe not what you were looking for. That’s, I would take 10 of those. If that means you get the one that really might change the course of a project. There’s a lot of great resources that go into helping teams understand and build psychological safety.

So Amy Edmondson has written on this extensively. I think she’s got a podcast through HBR. And there’s another book that I love called Turning People Into Teams. I think it’s by David and Mary Sherwin and it helps pinpoint like where team dynamics might be off and what activities might help those teams come back finding common ground and come back to balance.

Yeah. There’s like a series of small practices that you can continuously observe and experiment with. And I have brought that book into so many organizations now. And I can think of one time it made it from my desk to like a lead PM’s desk to an engineering manager’s desk. And everything is just actionable and tactical.

So really great resource to check out. But I think at the root of everything, you want to build a learning culture. It’s okay to have an idea that turns out to fail or to be wrong as long as you learn from it. And that makes it a lot safer to do that speaking up if failure is a learning motion. And you can support that on the team by directly asking for their input.

So make it really expected that everyone contributes their analysis. If you don’t hear from everyone in a meeting, like it’s okay to go out and call on people, give them that space. And for some teams, it might be easier to do this in writing than it is in a meeting. Some teams are evolved into more of a document culture, and that can be a great way to get everything captured.

And you can also model to the team that there’s an artist speaking up. I think I mentioned before, I just don’t like it. It may not carry the weight or get you the desired results. So you can help them understand how to bring rationale and really help people see what you see. Especially if your perspective is rooted in a different discipline that your stakeholders may not spend a lot of time thinking about, or they’re not as close to the customer as your team might be.

So reminding the team of the why behind the work needs to be repeated so many times, and then you can help them frame their arguments so they keep that bigger picture in mind. Once everyone has said their piece, there, it’s important to make that kind of reconciliation process, like the decision making process really clear.

So leaders definitely owe teams that, and expectations do need to be set that a decision will be made about focus at the highest level, and we’re going to stick to that. So it’s part of the commitments that you make as a team. I worked with a CEO once, he was amazing, and he said something like, everyone is entitled to share their opinion, but we’re not necessarily obligated to take it.

And that is the truth. There is going to be someone in that decision making seat. And so you bring your best and your most thoughtful perspective, and then hopefully that can get incorporated. I will say too, like sometimes leaders also just get too attached to having the idea for how a strategy gets executed and then they need to correct themselves so they can decide where things should end up in terms of the expected results.

But they do need to trust the teams for the what and the how. As a leader, you can really be a bridge between that higher why and helping teams understand, how their work attaches to that why. So that would be my last thought on that.

[00:16:56] Chicago Camps: Could you discuss some strategies or techniques that have worked well for you in simplifying complex messages while keeping the team informed and engaged?

[00:17:05] Helen Keighron: Something that really sticks with me, Lori Norrington, who is a very accomplished investor and a leader who have to sit on HubSpot’s board, did a fireside chat with the leadership community at HubSpot, and she really underscored that messaging takes a lot more repetition than anyone ever can possibly imagine for it to sink in.

And then guess what, this expands in relation to the size of the company. She also talked about the concept of cartoon clarity, which I love. If you think about a cartoon, it’s a couple panels, not a lot of real estate to work with. So you have to be able to really boil things down to the point where it would fit in those few panels where you could also think about it as if you were signing a billboard.

So people are whizzing down the highway and they need to get where they’re going and you want them to. Take away like one key message and imprint on that and then ideally one thing to do next. So that’s about the amount of time you have as somebody driving down the highway at 65 miles an hour. It’s similar to that in, in a workplace where people have flack pinging constantly and you just, it’s chaos.

Takes messaging across multiple mediums and channels for sure. So leading with that cartoon clarity and then finding the right moments to add nuance and deeper context, maybe an appendix. Thanks. But you are ahead of the game if there’s something that people can at least easily repeat. It is one of those things too where you may sometimes find yourself thinking, oh wow, like I have said this thing several times, I was not thinking, and a really common reaction is what’s wrong with the team?

But at that point you do have to get the mirror out and look at yourself, take a hard look. And start testing your message out with different groups to make sure it’s clear. It’s really fine to say, even to someone on the team who might be a few levels down from you, help think of an even better way to say this.

And obviously a huge shout out to my content designer friends. They are very often being exceptional at this type of distillation. Once you’ve experimented with the message and you can feel good about it, you’ve leveraged culture to keep reinforcing it too. So find your local champions and your storytellers and your organization.

It doesn’t just have to come from the same set of leaders. In fact, it’s better if it’s around sound. And a lot of times people just don’t. Neglect to properly enable line managers with the right messaging and objection handling points. So those are people that are going to hear the issues from their direct reports first, and they need to be really empowered with the right talking points and also a way to pass back what they’re hearing to other leaders in case there is a problem with the message.

That’s another way to diagnose it really easily. I’m a big fan of just writing things down for kind of clarity of thought. Having a written comms plan can really force your hand to make sure like you’re considering all aspects of the message and how it spreads. So starting with just who’s being impacted, what are they being told?

When are they being told? How do they find out? And so for a really complex message, like around, Hey, we’re launching our strategy or we’re having some major organizational change. You might have a really multi pronged approach. So you might have a TLDR summary and it gets posted on Slack, which links to a longer explanation.

The leadership is probably recording videos and I’ve gotten a lot of mileage out of Looms and other organizations because it’s just so much more personal. And then there’s probably going to be enablement behind that. So there’s going to be follow ons like maybe a town hall meeting or managers might break out and meet with their functional teams.

But even simple things require alignment. So take a team move. If that communication happens out of sync, people tend to spiral out of controls. You could always tell comms went well, if you put the effort in and then you get back, okay, cool. That makes sense. That’s amazing. That’s the best possible outcome.

You want things to be well understood, like non events. And you can tell it didn’t go well when people start peppering their managers with questions and objections and even filling in their own narratives because there just wasn’t enough clarity or people got the message out of the wrong sequence. And I’m sure we’ve all been there and that takes you so much time to clean up.

When it probably could have been handled in a different way with just, I don’t know, five minutes more planning.

[00:20:58] Chicago Camps: Could you share an example from your experience where achieving alignment within a team was particularly challenging and how you navigated this situation?

[00:21:07] Helen Keighron: Just to set the scene a little bit, there was a group of related teams.

Who were building a brand new product. So this was something that had not been executed before within the company. It had high technical and regulatory complexity and it needed to be a whole new experience, but also interact really seamlessly like with the existing platforms. There had been a lot of upfront work that had been about like technical proof of concepts just to make sure it was feasible and get the wheels turning on these compliance activities that this team was not used to normally dealing with.

And it was actually really clear what we would need to see from a business perspective. So in this case, there was a very strong strategy. It made a ton of sense, but we had executional confusion because they were dependencies with even other teams and other orgs who are going to need some primitives from this team.

And what also hadn’t happened was defining the actual experience. Individuals, teams really weren’t sure what part do they build next or in what sequence. Everyone could see like their own part of the elephant that they own just based on the codebases and kind of the missioning of the team, but nobody was really sure how to fit it together.

So we had lots of problem statements about different aspects of what customers needed, but we had to tie it together. Teams were also hyped to work on the overall launch and they wanted to move really fast. But this was the kind of work that was going to need some connective tissue. We had the team topologies right in some sense and that these teams could then go make progress independently really rapidly to deliver value once we had that alignment.

But there was pretty big foundational questions. So the way we decided to address that was get a subset of members of these teams together. And just make some more federal decisions about the platform as a whole. The way we express this, we did a design sprint and we started by creating a system map.

So to really just understand and describe the relationships between. All these different data objects and services that would need to be built based on how customers were actually expecting to use this new product. We consumed and synthesized an amazing body of some background generative research that our researcher had done.

And then we went through a light version of OOUX activities, object oriented UX is OOUX and Sophia Prater, who really coined that had just come to spoken to the team and gotten them really excited about that methodology. So the net was, we all brought our own version of here’s how we think the system works.

Here’s what we think the map of the world is basically. And then we reconciled and we drilled that down to a single working model. And then we built out a few major flows, including how some of these pieces of data would intersect with existing real estate in the product. And then we had rapid iterative testing of just these clickable lo fi prototypes with customers.

And people say, you can’t test wireframes or you have to show things with a high level of visual polish. But in this case, we just set the expectation with the customer that you’re going to see something that’s pretty bare bones. And then we just literally changed it between customers. And by the end of this process, over a day or two, we were able to draw out some, pretty differentiated conclusions about what their needs might be.

And then that kind of informed like a whole order of operations to see, okay, here’s a sequence for building out these different components and that ended up feeding a roadmap. And what was important here is that we hit work really quickly. And then on the communication front, we had to do a ton of stakeholder communication and management.

Not everyone had the bandwidth to come and sprint with us. So what we did was regular kind of micro shareouts along the way, which was usually like a quick loom and a summary and a Slack post, just in the main working group for that team. And people were able to get a lot of input along the way, feel like their thoughts were heard.

And then when we presented as a final kind of stitched together version and like the customer insights, it was pretty non controversial. So the actual process was basically we just reached into everyone’s head and pulled out the information and started synthesizing things. And then we had pictures to point to so people could actually visualize the end experience as opposed to just the reams of words and documentation that hadn’t existed before.

It was a really fun process. It was a fast process, but it got us over that hump of teams just not knowing where to start.

[00:25:00] Chicago Camps:As teams grow and projects evolve, alignment can sometimes slip. What are some signs that a team is losing alignment, and what immediate steps can you recommend to realign?

[00:25:11] Helen Keighron: This is a good one.

Ideally there’s some kind of standard for reporting out process, and I am not saying you need some sort of rigorous kind of thing. It can be pretty lightweight, it might just be encapsulated in whatever system the team is using to track work, like whether that’s JIRA or something else. So no perfect method, but what you’ll start to see is things get vaguer and vaguer, like in readouts, in tickets, you’ll see like a stall in progress.

Basically, you might also hear some tensions. You might hear even some finger pointing at other teams sometimes. And what I would say is, do not just talk to your own function. Keep those cross functional relationships going constantly. So make the rounds and be like what are you hearing? What are you hearing?

Keep an eye out for the team kind of feeling frustrated or disengaged in any way. Okay. And I really value making time to speak directly with the ICs who are doing the work on a regular basis, whether they’re designers or engineers or product managers. And just try to get almost like an early warning system for what might be going on in that team.

You really do have to do the diagnostics to see what’s going on. No one person’s story is going to be accurate. The truth usually lies at the middle of several stories. But you want to understand what’s the possible reasons behind like the symptoms that you’re seeing. The examples can be pretty interesting.

You might find out that you have a manager who did the disagree part but not the commit part and they’re transmitting that attitude like to their team in some way. Okay. Teams could be receiving conflicting feedback from different stakeholders. There could be unaddressed functional conflicts. Like maybe engineering always feels like they’ve got a rush and they’re feeling resentful.

Or maybe design doesn’t feel like they have enough ideation time and they’re getting pushed to throw solutions over the fence before they feel like they’ve had enough time to, to release it with them. And then sometimes things happen where new information becomes available, which is great. But what’s not great is if you don’t have a mechanism for surfacing that and really realigning back to the plan.

So that goes back to the culture in this like safety piece that we talked about and not making extremely rigid plans because people should be rewarded for bringing new findings to the table, even if it means the plan has to change. There’s probably a very good reason. for the plan to change. And if people are not comfortable bringing that, then that can cause a lot of just swirl on teams.

So in terms of some tactics that you can use, obviously it’s always a great time to realign to vision and strategy. Has there been a change in the flow of communications? Maybe you need to get a little bit of a drumbeat cadence going with reiterating some of the things. I would also say discuss it really openly and just bring curiosity into the conversation.

I’m noticing that we might have a disconnect between Team A and Team B because I observed this set of behaviors. So help me understand why the perspectives are different. So you’re not accusing anyone, you’re just saying, here’s what I noticed, and you’re letting somebody have the floor and tell their story.

You can also make a timeline. This is one of my most basic tricks in the book. But when something has gone off the rails, make a timeline. Detective Pikachu goes back and stitches together. Can we pinpoint when something changed? So maybe a team actually decided things were going so well in collaborating with another team that they actually stopped meeting regularly.

And there’s been some, let’s say some drift since then. You can also define roles and responsibilities if necessary. So DACI is a format I’ve worked with quite a bit. So the D stands for the driver. Who’s the person who drives the decision. The A stands for the person who makes the decision, the approver.

And then C is for contributors, people or teams whose work or knowledge might Help move the project forward. And then I is for inform. So people whose work could be affected in some way by these decisions and should be kept in the loop just to make sure that everything is going to go smoothly. It’s also sounds really obvious, but sometimes they’re just a lack of a shared space for documenting decisions.

It can be as simple as if you’re a designer keeping a decision on page. In Figma. So you can trace the provenance of the choices that you’ve made, or potentially it’s in a ticket or it’s in a confluence page. So that’s a really great place to have a trail on history of the project. And sometimes teams just need help breaking harder problems down into smaller milestones and they’re churning because they’re thinking about something that’s almost too big to get done and they’re losing sight of the original goals because they have some sort of Taj Mahal in their head.

And really what you need at this point is like a log cabin just to get to the next stage. And finally, what I would say here culturally, take the time to celebrate what’s going well so far, like people just need to hear it and frequently, like in many company cultures, we get really busy, so we point out what’s not working and then it’s assumed if you don’t hear about it, great job for you.

But one of my favorite memories was we were launching our commerce product at HubSpot. And we had a team gathering at a major release milestone and we did an anonymous forum where people could just hype each other. So the team also took a shared day off, which is nice because then you’re not coming back to Slack messages and emails and things like that.

But before they did that as a send off, we gathered together and we read through the feedback and people just said the nicest things to each other, like across teams and across departments. And everyone left smiling with just like this renewed sense of appreciation and just like gratitude. Sometimes just remembering Hey, we all actually each other.

Like things can get hard. I will say at the end of the day, like alignment health, it comes down to strategic clarity. The team operating system plays a role. The team culture plays a role. And that includes how you plan and discuss issues as they arise. And then your org structure and team topologies are going to have a huge influence.

And then the communication skills of leaders impact literally all of these theses. So sometimes you can get things back on track with just a few conversations and really targeted instead of like smaller interventions, but you really want to keep your head up and be looking for are there patterns that are happening again and again, like across multiple initiatives.

And it may be that you need to work with your cross functional partners or manage up and consider whether some bigger interventions actually need to happen.

Event Details
Keeping the Team Together: Lessons in Leadership and Alignment
June 17, 2024
5:00 pm
June 17, 2024
6:00 pm
Tent Talks Featuring Helen Keighron Keeping the Team Together: Lessons in Leadership and Alignment Join us for a thought-provoking Tent Talks session with Helen Keighron, a seasoned design executive and startup advisor, as she explores the concept of “alignment” within...


July 2024