Notes

Several years ago, we developed a robust e-commerce audit offering. It is a lower bar to entry for clients who can't afford a website redesign and a great option for clients only looking to improve upon their current website. In the audit, we dig into website performance, UX, and tech, share our findings, and develop a roadmap to make optimizations and improve conversion.

What I find fascinating about a website audit project is the problem-solution mentality. We do our best to understand the client's business to be able to identify the website's issues and come out with actionable insights. Lately, I've been interested in the contrast of this approach alongside our process for website redesigns.

When working on a website redesign, the client's sentiment is often different than an audit. They're not concerned with fixing, so there's less focus on challenges and more focus on reinvention. "Our website doesn't represent our brand, don't look at it." We have to be careful of blindly throwing everything out. What works today? What doesn't? How will the new website tackle these challenges and bring added value?

I'm eager to experiment with different ways of bringing the spirit of website audits to website redesigns. I don't ever expect these two types of projects to be the same; however, I think there's a lot to be gained by anchoring ourselves on the same mindset.

This post originally appeared in Edition No. 080 of my newsletter. Subscribe here.

I remember applying to a designer role at Barrel almost nine years ago. Of course, I was excited about the work and what seemed like a tight-knit team, but the ping pong table, happy hours, exposed brick office walls, beer on tap, and dog-friendly vibe screamed "cool." If you asked me what culture meant back then, I would have mentioned those perks.

As my role has evolved over the years, Barrel has, too. We've created new positions and introduced services. We've sunsetted some of those same positions and services. When the ping pong table started collecting dust, we used the space for a content studio. We expanded our office, and under a year later, we started working from our beds and kitchen tables.

At this point, Barrel is a team distributed all over the world. Day in and day out, I work closely with co-workers who have no idea if I'm 6' 5" or 5' 6" (spoiler: I'm just under 5'8"). While I can't wait to get our team in one room, company culture is about more than perks and evening drinks.

An employee recently shared feedback that they see an opportunity to boost morale and strengthen connections with their co-workers. When I first heard this, my mind wandered to visions of Barrel circa 2013 - ping pong lunch breaks and karaoke happy hours, trying to brainstorm what else we can do beyond half-day Fridays, game nights, and team workshops. We'll likely have an off-site sometime this year, but will that really make this person feel better long-term?

The reality is that perks and events may create deeper connections, but what carries the most weight? The work. An agency's company culture centers around the work. That's why we're all together in the first place — to deliver work we're proud of that drives results for our clients. When we can't achieve this and do it with a smile, that's a sign that the "culture" might need a boost.

In my essay "Conducting My First Upward Feedback Survey," I defined company culture as:

1. How we work (process)
2. How we work together (collaboration)
3. How we feel while we do both (camaraderie)

If I view our company culture through this lens, I couldn't agree more with the employee's feedback — there are clear opportunities to improve how we work. Right now, the blockers and communication gaps are making collaboration tough, and in the end, camaraderie suffers.

I'm not discounting the power of getting to know your co-workers through non-work activities. However, if we're feeling strained, uninspired, or unable to be effective at our jobs — happy hours, perks, and ping pong are not the solution.

I've enjoyed getting into the day-to-day projects over the last several months and am excited to continue working alongside the team to improve the way we collaborate. It's inspiring to see the team rallying around innovation and experimentation. In many ways, I think the challenges we're working through together now will make us that much stronger down the line.

With all of that said, I think it's important to remind the team that we're not performing heart surgery. Creating space to laugh together, take a deep breath, and sometimes, just hang out and talk can go a long way.

Speaking of my early days at Barrel, a developer who taught me a ton about development when I started is re-joined us today as Director of Technology. It's awesome to have Scott back at Barrel.

***

This post originally appeared in Edition No. 080 of my newsletter. Subscribe here.

One of the challenges we see on accounts is the time it can take to get back to a client on a request, especially when it is technical. There are different reasons for the delays, but a common one is how long it takes to estimate work.

Here is an example interaction with a client, along with the inner dialogue of the team.

• Client: We feel like we should give customers the ability to customize their bundle. Can we add that to this page?
• Team: (Uh oh, that is not in scope! Scope creep sucks. I could tell them it's not in scope, but maybe we can make it work. I'll feel better telling them when I know the effort). Interesting. That makes sense! It will definitely offer customers more variety. We can get back to you on the effort to add this feature.
• Client: Sounds good.

A client recently told me how often she and her team throw out ideas during our meetings. They do it to brainstorm, and when ideas seem worthy, they're curious to understand what's possible. In her words, "a gift message option seems cool, but not if it costs $10k."

When the above dialogue happens, it takes us days (hopefully not weeks) to come back with the $10k price tag. The client may decide to move forward or put it on hold. Sometimes, the client feels frustrated because they thought the work was in scope, having discussed it in a meeting. If I'm not closely involved in the work, this is where I end up getting involved.

Last week, this scenario came up. After chatting with the team, I realized that we're not estimating the work to figure out if it is in scope. We're estimating to get to an accurate number. However, from the start, the team knows whether the request is in scope and roughly what the effort may be. This is where the "gut check" comes in.

Rather than jump to estimation, there's an opportunity to dig deeper to understand the context of every request. Is it an idea or a business need? From there, we can use our gut to anchor the client if the request still makes sense.

• Client: We feel like we should give customers the ability to customize their bundle. Can we add that to this page?
• Team: Interesting, it would offer customers more variety. Is this a request you currently hear from customers?
• Client: Not really. We think that a first-time customer could benefit from a sampler vs. committing to one flavor.
• Team: Ah, a sampler makes sense. From a logistics standpoint, could you offer a sampler now?
• Client: We could. Maybe that would work.
• Team: Oh, great. Based on what you've told me, a sampler bundle seems like the right approach. However, let us know if adding bundle customization is a priority. It's not currently in our scope, but my guess is that it's at least a $15k effort.
• Client: Ah, I see. I thought it was fairly simple. Let's hold off on now. We'll let you know if we decide it's a priority.

In this exchange, the team and client know exactly where each other stands. By getting curious, the team understands the background of the request, so the scope discussion is that much easier. The team may not know the full effort needed to complete the task, but anchoring the client helps them align on what's important and what next steps make sense.

This post originally appeared in Edition No. 079 of my newsletter. Subscribe here.

One of our recent initiatives is rolling out more stringent hours reporting across our retainer contracts. The goal is to make sure the client understands where their time is going, and we can get ahead of potential overages. However, hours reporting doesn't matter if we don't set the right expectations on hours from the start.

When we're working with clients who have a lot going on, it can feel like we're constantly getting hit with last-minute requests. Under the pressure of time, we rush to get it done. If this results in overages or delays on other tasks, the conversation with the client is not easy because it's after the fact.

As we continue to introduce hours reporting, there's an opportunity to better align with clients on their initiatives each month. We're currently experimenting with Asana to get that alignment, but we're open to seeing what format works best for clients.

No matter the tool, imagine a 50-hour retainer planned like this: 10 hours for product page updates, 20 hours for landing page, 15 hours for email designs, 5 hours for content population. Maybe I'm optimistic, but if the client knows this plan, I believe we can minimize last-minute, urgent requests. Clients won't blindly ask for something new without acknowledging how it will fit and how priorities need to change.

This post originally appeared in Edition No. 079 of my newsletter. Subscribe here.

This section title is probably no surprise for anyone who has been following my newsletter for a while. In a world of text messaging, Slack, and social DMs, I find the casual nature of everyday communication to be often more challenging than it is helpful, especially in a team setting.

There's no distinction between urgent and non-urgent messages. Important decisions get lost in threads and conversations that look more like a CVS receipt. In the end, people lose focus, consumed by a never-ending Slack exchange that goes nowhere. While at the same time, mission-critical questions get missed. They jump on Zoom to sort it out, and suddenly, the workday is over.

What I love about email is how it promotes slowing down and thinking.

You could

sned an

send*

email that

looks like

this.

But you don't.

You prepare what you want to say. You consider how you want your recipient to feel when reading it. You aim to strike the right tone. You try to deliver a clear message. You write, you re-write. Sometimes, you ask someone for a second opinion.

Getting involved in all kinds of moving parts on projects last week, I took to email to keep the team aligned and on track. I realized I'd been promoting the power of email among the team, noting how it would become contagious when people saw its power. It was time to practice what I preached.

After every meeting, I forced myself to write a follow-up within 1-2 hours, documenting key topics and decisions. I also captured follow-ups and delegated the next steps with deadlines. Sometimes these emails were long, but they were clear. They could also act as a reference for any future decisions or questions.

Throughout the week, key project team members who couldn't attend some meetings I was leading shared how helpful these emails were in keeping them aligned. In one case, a team member did research to prepare for our next meeting without talking to the team, not on Slack, not on Zoom, not even on email. By the end of the week, it was great to see others taking a similar approach, documenting decisions, and moving other follow-ups to email.

I ended up closing out the day at 9:45 pm on Wednesday. Writing an email was the last thing I felt like doing, but the alternative looked more painful. I knew that if I didn't take the time to capture my thoughts, the team would be ill-equipped to keep going. They'd end up reaching out on Slack, and if I didn't catch myself, my recap and follow-ups would end up spread across DMs. We may even get stuck in a back and forth for another hour!

Sending an email may seem simple, but it takes effort, and the lure of a sloppy, quick message on Slack is real. But once you get in the groove, the effort upfront is a game-changer, not only saving you time but everyone else time down the line.

This post originally appeared in Edition No. 078 of my newsletter. Subscribe here.

What started as a joke early in the week became a phrase I rallied the team around. Act Natural. Too often, we get caught up in our heads, worrying about how a client will react to a conversation or a co-worker to feedback. We enter the interaction full of anxiety. We stumble over our words, and in the end, we create the reality we hoped to avoid.

There were moments last week when I saw myself heading down this path. But it wasn't until I saw others in the same boat that I recognized the pattern. "Act natural" was a fun catchphrase to say lead with confidence, enter situations with poise. Offer recommendations, not options.

In one instance, we discovered that a client needed to upgrade one of their accounts to launch the work we completed for them. Without understanding all of the features yet, we didn't know this at project onset. The team was concerned that the client would be unhappy with the price of upgrading and started concocting a Plan B, which required compensating hours and rebuilding the work. In the end, we held off on sharing Plan B; instead, we recommended the upgrade and explained the long-term benefits. The client was understanding and agreed with our recommendation.

I look back on this situation and can't help but cringe when I think of what might have happened if we ran with our Plan A/B approach. We'd take responsibility for an issue that wasn't an issue. Not to mention, we would have overwhelmed the client with options. Sometimes, it's easy to forget that clients hire us to be their guide. We mean well when we give options, but options put the onus on the client. They often want to say yes or no and move on.

I'm not suggesting that we should not have a backup plan if a situation goes awry. However, there's a difference between having a backup plan and entering situations expecting the worst. Act natural. Remember that everything happening is happening. Act with current facts, not where we once were, to provide a path forward and shape the desired future.

This post originally appeared in Edition No. 078 of my newsletter. Subscribe here.

It's been about five months since our move to Pennsylvania, and finally, we have a bed. No more sleeping on a mattress on the floor! The short story is that we found a bed we loved, but it arrived damaged. Twice. So, we gave up and looked elsewhere. We finally found a different bed, and it got delivered last Tuesday. We couldn't be happier. So, why am I sharing this? Let me explain.

When the delivery showed up, I asked if the guys would wait for me to unpack the items before they left. I didn't want to get stuck with a damaged bed for weeks again or make them come back.

Before I knew it, the delivery guys were unpacking the bed in the driveway, bringing in each piece one by one. It seemed like this might have been a common practice, but I couldn't help feeling like I was making things complicated.

As they left, I wondered, when else have I approached situations with the baggage of past negative experiences? Different bed. Different brand. Different delivery company. Yet, I didn't feel comfortable taking my chances with them.

The whole situation reminded me of a client who seems to question every suggestion we make. Or a stakeholder's request to print out websites designs and mail them to their office (true story). To us, these situations may seem odd, annoying, or crazy, but there's always more to the story.

In this case, I offered up my context, sharing why I made the original request and how much I appreciated their help. I didn't want the delivery guys feeling confused and thinking, what is up? Unfortunately, not everyone offers this context openly. Sometimes, we have to dig.

Once we do, we find the questioning client got burned by a past agency. Why are we sending websites in the mail? The client likes to be hands-on and finds it easier to give written feedback (and send pictures of mockups cut up and pasted back together).

I find there's freedom in this understanding. It helps us stay focused on the work, free of judgment, and opens the doors to new ways to create value. Maybe it's inviting the nervous client into a workshop where they can feel more involved or showing the print-loving client how to annotate on the web. These small actions can go a long way and set us on the path to a long, fruitful collaboration.

There's a saying among motorcyclists that goes something along the lines of "the bike goes where you look." It's a phenomenon that I wasn't on board with until I experienced it firsthand while learning to swerve. Luckily, I was going 10 mph in a parking lot.

When you're on the bike, making a turn, or just riding along, the path you follow will be the one you're looking down. On a beautiful day without many vehicles on the road, this concept may seem pretty straightforward and easy to master. However, the windier the road or more vehicles around you, the more surprises to encounter, the harder it gets.

Let's say a deer walks out in front of you, or you make a sharp turn and notice a giant tree close to the road. Often, in these moments of panic, our instinct is to look at the obstruction while we contemplate how to react to it. When this happens, our hands unconsciously steer the bike in the direction we're looking, and well, you can assume the rest. I don't have any scientific explanation to share but trust me — you go where you look.

Whether or not I'm riding a motorcycle, I've caught myself fixating on roadblocks, not the way forward. While it is helpful to get clear on the challenge, letting it dominate our focus gets us nowhere. When everything is calm and going our way, there's no way to look but ahead. Then, our plan doesn't work out, a client expresses concern with our work, or an employee is underperforming. In these moments, it's all about where we look. As a leader, I've learned the power of keeping myself and others centered on where we want to go, not what's getting in the way.

I recently had a conversation with a manager on my team about one of their employee's performance. The manager was in the process of writing this person's semi-annual review. They shared some concern that elements of the feedback were the same as the last two reviews. Here was an otherwise stellar employee who could not shake this one piece of feedback.

As the manager told me more about how past conversations about this feedback had gone, it became clear that the manager had become fixated on the deer, not the way around it. Rather than help the employee see what they were capable of, they continually reiterated what was getting in the way. This fixation created anxiety for the employee, constantly caught up on the roadblock, not seeing where they wanted to go. I worried that, at some point, this would become a self-fulfilling prophecy, and we'd lose a great talent.

The manager and I left our discussion with a commitment to change. Rather than attempting new ways to give the same feedback, they would align with the employee on their desired future. As the manager, this approach helped them be a better guide. As the employee, it showed them what was possible. They could breathe and focus on doing their best work, not trying to solve a problem.

"You go where you look" has become a bit of a mantra for me — on the bike, in my work, and in life. It's a pleasant reminder that there's always a brighter path ahead, it's just up to me to see it.

Since I started riding a motorcycle, the most popular comment among friends and family is: "I'm not worried about you; it's everyone else on the road." I remember hearing the same when I was learning to drive a car. Had I not gone through the motorcycle training course, I may have shared this sentiment. Now, it feels like a hopeless outlook. 

I get it, though. It's another way of saying, "I trust your ability, but not the million other drivers out there." But at the same time, it suggests that I am the victim of my surroundings, and if something goes wrong, there's always someone else to blame.

I prefer to adopt a different perspective: I am in control.  No matter what comes my way, the outcome will come down to what I did or didn't do. ‍

When I flick the starter on my bike, I'm encouraged by this mindset. It invites me to do everything in my power to ensure a safe ride. Taking this level of ownership also provides an opportunity to learn and improve, rather than blaming conditions that are "out of my control" and repeating the same unwanted outcomes. It's the difference between blaming the driver ahead of me for stopping abruptly and admitting that I was following too closely behind. The former teaches me nothing. When it comes to leadership, I believe in the same approach.

Leadership means taking ownership over your decisions and actions, and as a manager, those of your team.

The other night, I took my wife, Dana, to try a local restaurant to celebrate her birthday. We ended up chatting with the rmaître d' who was filling four or five roles at once due to being short-staffed. He and just three other employees were serving 100-some guests on their own. He mentioned that they have had a tough time finding experienced help and went on to tell us a funny anecdote about a young kid they recently hired. Let's call him Sam.

On Sam's first day, the maître d' asked him to go around the restaurant with a pitcher of water. So, that's just what Sam did. No, not filling any cups — simply walking around with the pitcher.

It's no surprise that the maître d' was frustrated. He vented to his manager, who replied with this: what did you ask Sam to do? The maître d' realized it wasn't Sam's fault; it was his own. He hired Sam with little experience. Eager to do a good job, Sam loyally followed the maître d's instructions to a tee. 

The maître d' sat in silence, regretting the harsh feedback he had already given Sam. By taking ownership over the impact of actions, the maître d' saw an opportunity to improve his communication with all the wait staff, chat with Sam and help him get better.

I can empathize with the maître d' on many levels. Whether it's an employee poorly handling a client situation or a project going off the rails, it's easy to place blame and analyze everyone else's behavior. However, when I stop and look at my involvement, I always find there's more to gain.

As a manager, I sometimes struggle with navigating conversations where a direct report shares their experience dealing with an issue that I know is an issue but is large enough that it will take weeks or months to feel progress. I don't want to leave them hanging or downplay the situation to try and make them feel better. So, I listen. But, at times, I feel helpless. It can feel as though bricks are piling on my back one at a time, then soon enough, it's hard to walk.

I shared this experience with Chris, my coach, earlier this month. He responded with this: the person who offers the most hope is the one with the most influence.

All month long, I've carried this statement with me. I've even shared it with some folks on my team. It's a reminder that I don't need to provide a quick-fix solution to be a leader for my team. Nor should I become consumed by seemingly urgent issues. Instead, I can acknowledge the current reality then anchor the conversation on the future vision and provide hope. 

Hope helps us see that our challenges today are temporary, and frankly, the journey to overcome them is worthwhile. It means we'll achieve a brighter tomorrow. Without hope, we lay in bed at night, sleepless, asking ourselves: what's the point?

In keeping with the brick metaphor, Chris urged me to take the brick off my back, look to the future, and ask my direct report, "How can we lift this together?" It's no longer about me solving the problem alone or asking them to go figure it out. It's about working together to see what small steps we can take today to ensure long-term progress tomorrow.

Prior to hiring our Director of Client Services, Kate, our client relationships were managed by the Barrel partners or our Director of Business Development, Dan. In some cases, this worked well. In other cases, we missed opportunities to have meaningful conversations about our clients's businesses, ways of working together, and opportunities to better support them in achieving great outcomes.

When Kate joined, we officially introduced the Client Services team. Since then, Kate has been instrumental in bringing energy and momentum toward a future where account management and client service are unparalleled.

As we onboarded Kate onto existing client accounts, the partners took a backseat. We thought that staying too involved would not only confuse the client on points of contact but might get in the way of Client Services' ability to own the relationship. We did our best to transition Dan's accounts to Kate.

Flash forward to the present day. Our Client Services team is growing and almost every client is represented by Kate or an Account Director. However, we're noticing a gap.

Every client has a different set of stakeholders with a range of titles. But if we generalize for a moment, it is simple. There's the day-to-day contact and the day-to-day contact's boss. Sometimes, the day-to-day contact's boss has a boss, too.

In a nutshell, an Account Director's job is to:

• Make sure Barrel is delivering on what we set out to do
• Coordinate the Barrel team
• Solicit and address feedback
• Identify opportunities to better support the client

More often than not, an Account Director is working directly with the client's day-to-day contact. They may get face time with their boss, but these conversations often include other team members and focus on the work.

The gap is a missing dialogue around Barrel's performance as an agency and insight into the client's future trajectory. How is their team evolving? What is their top priority this year? Next year? What opportunities do they see? Where are they investing resources?

To make progress, we're experimenting with introducing an Executive Sponsor to every account. An Executive Sponsor can be a partner, Kate, or Dan. No matter who they are, they are a designated Barrel representative to periodically facilitate one-on-one conversations with the client's key stakeholder, typically C-Suite.

In some ways, the Executive Sponsor can act as a third-party participant, offering a unique perspective without being caught in the details of the day-to-day. They are there to listen and offer up ideas on how to strengthen collaboration.

For existing accounts, we will align on who will be the best rep. A number of clients already have an informal "executive sponsor" who acts mainly as an escalation point. This roll-out will simply confirm their role and open the door to additional conversations. For new accounts, leadership will look for opportunities to connect with key stakeholders early on to establish a relationship for future check-ins.

Prior to one-on-ones, it is critical that executive sponsors touch base with the internal Account Director for any recent developments of the account. The Executive Sponsor can use these points to solicit feedback during the conversation.

Some questions an Executive Sponsor might ask:

1. Thinking back to the start of our most recent engagement. Do you feel like we're on track for what we set out to do?
2. What have you appreciated most about our relationship? Where do you see an opportunity for improvement?
3. How could we improve the communication and collaboration between our teams?
4. Have there been any moments on the account that you think I should know about? Positive or critical?
5. What are you most excited about for the future of your business? Most concerned?
6. Where are you investing resources for next year? Any important initiatives in the works?
7. If you could wave a magic wand, how do you wish Barrel could deliver results on your key initiatives?

We're looking forward to kicking off this initiative with the team and seeing how it evolves in the coming months.

We talk a lot about outcomes at Barrel.

The outcomes our clients want to achieve as a business and as a brand.

The outcomes we want to achieve together as a team.

The outcomes we want to achieve as an agency.

In this context, an outcome is the desired result of our efforts. When we're scoping new business or kicking off new initiatives, it's easy to forget about outcomes as we attempt to map out the "perfect" process. We become consumed in WHAT we're doing without considering the WHY. An outcome is the WHY.

When we go down this path, we start making decisions based on personal preferences and risk missing our target. We become task-masters, thinking that if we can just get the task done right, we'll be good.

An outcome is:

• Client: To increase the average order value (AOV) of a client's commerce website.
• Team: To create an environment where feedback is welcomed and wanted.
• Agency: To attract X number of qualified leads per week.

An outcome is not:

• Client: To organize a UX immersion workshop.
• Team: To invite a feedback expert in for a workshop with the team.
• Agency: To launch a beautifully designed landing page on the agency's website.

Why Outcomes?

There are a number of benefits to focusing on outcomes. Let's take a look at a few I've experienced.

Promotes learning

Consider a person looking to get fit and healthy. If they choose to hire a personal trainer, they don’t do it because of the nuances of their programming. If during the sales process, that's all the trainer talks about, the potential trainee may appreciate the trainer's enthusiasm for fitness but wonder if they can actually help them. In contrast, if the trainer gets curious about the trainee's outcomes and shares how they've achieved similar results with others, the trainee is bound to hire them.

By focusing on the trainee's outcomes, the trainer may also find that their typical process may need to evolve. Perhaps the trainee has a background lifting weights and won't need the same basic training upfront. By re-thinking their process, they'll not only learn something new, but they'll get better results.

Outcomes push us to look beyond ourselves. When we take the time to understand an outcome, we're forced to seek out new perspectives and question what we know. The more we focus on outcomes, the more we re-think old beliefs, and the more we learn.

Invites innovation & experimentation

The beauty of outcomes is that they anchor us on a future result, not the path to get there. Outcomes give us the permission to experiment. Sure, we may have a proven process or set of best practices but if along the way, we face an unforeseen challenge, we'll be ready to pivot.

Let's take the example mentioned above. Let's say that as an agency, we're looking to amplify qualified leads coming in each week. We do our research and discover a landing page template that has generated results for other agencies. Within a week, we design and launch a new landing page that speaks to our positioning.

Over the next few weeks, we see some uptick in qualified leads but not at all what we were hoping for. We don't give up. We don't change the copy and hope for the best. We realign on our outcome. We dig into what it means to be "qualified" and discover that there's a gap in understanding where clients see the most value in our partnerships.

We decide that interviewing key clients and getting their take on the landing page may generate helpful feedback. These insights inspire us to test multiple landing pages and target new type of potential clients. In the process, we go deeper on the services that our clients find most valuable. We not only end up generating new qualified leads but grow existing accounts along the way.

Encourages ownership

There's an innate sense of ownership that comes with centering ourselves on outcomes. As a manager, I see this every day.

There have been times where I lay out a process that I think will achieve a result. I anchor the team on what needs to happen at every step and how to move the process along. The trouble with this approach is that the team is more concerned about doing WHAT I asked them to do, not WHY they're doing it. When they hit a roadblock, they're lost, looking for the user manual on how to troubleshoot the issue. Well, unfortunately, the manual doesn't exist!

By shifting the team's focus from the process to the outcome, the team can take ownership of the work. They're no longer trying to get it "right," they're working together to achieve results. They're not only encouraged to experiment and innovate, but they understand how their efforts align with a greater purpose. This ignites a hunger to find the opportunity in setbacks and a passion to see the project through, no matter how the journey unfolds.

One-on-one time with employees, especially direct reports, is precious. But what happens when it feels like there’s nothing to talk about? Do you end early and give them the time back?

I remember asking myself this question during a one-on-one a number of years ago. It helped me see that it was up to me to create value in my one-on-ones; I couldn’t rely on the employee I was meeting with. That meant that I needed to come prepared with questions and a clear idea of what I hoped to create during our time together. Not every employee is an open book, especially when they're new.

The aforementioned one-on-one was with a junior designer for their 3-month check-in, a ritual at the time to get a read on how new hires were settling into the team and role. For the purpose of this story, I'll refer to the employee as Melanie.

We were at the office meeting in a conference room known as The Cellar, a dimly lit, brick-walled room housing the stash of bourbon that we poured on Fridays to toast to the week. Since expanding our office's footprint a few years ago, we sadly said goodbye to The Cellar.

Melanie was a particularly positive person. Always smiling, even in the face of a new hurdle. Despite having just joined the team, her fellow team members were already remarking on how she brought a lightness to tense situations.

I kicked off our conversation with a simple question, how are things going? Eyes wide with optimism, Melanie responded, "Good." I'll admit, I was hoping for more… just good? Silence filled the room and my mind wandered to second grade. This must have been how my parents felt when I came home from school.

• Mom: How was your day!?
• Me: Okay...
• Mom: Just okay?

Melanie and I had an hour blocked off. There had to be more to discuss than "Good!" I reminded myself why Melanie and I were meeting in the first place. How is she feeling about her work? Her role? Working with the team?

Just days before, I chatted with the lead designer on Melanie's current project and heard that it got off to a shaky start. I used this as an opportunity to dig in and asked: How has your experience been working with [lead designer] on your current project? She went on to talk about how much she enjoyed the project, a positive take as expected.

As Melanie's described her enthusiasm toward the project, I wondered if she sensed the same shakiness that the lead designer had. I was upfront about my conversation with them and asked what Melanie felt contributed to the last-minute feedback and late nights.

The same hour that once seemed like it might be a long painful trek now felt like a sprint. We were moving fast and without any time constraint, probably would have gone for another hour.

By the end of our conversation, we had uncovered areas of opportunity for Melanie to grow as a collaborator and even identified a few pieces of feedback for the lead designer. Feedback that otherwise would not have been discovered and therefore, never shared.

I've carried this experience with me for some time now. That one hour with Melanie underscored a lesson that I was used to applying when working with clients but hadn't yet considered as a manager.

If I lead with ambiguity when talking to my direct report, client, colleague, friend, wife, family, or future child, I can only expect more ambiguity in return. To create engagement and value, I need to first know what I'm looking to achieve and then, be specific.

It's the difference between "How is your day going?" and "You had a big presentation this morning! How did the client react to our insights?" Both help get a sense of the employee's state of being, but the latter inspires detail and can be a great jumping-off point for a much deeper conversation.

A few weeks ago, I learned a valuable lesson after chatting with co-workers. Let's call them Jared and Joan. I meet with Jared and Joan weekly, so we are comfortable being open with each other and speaking freely. Jared was dealing with a situation I'd dealt with in the past, so I felt like I might be able to offer some helpful advice. After he talked through what was going on, I jumped in to provide insight.

One piece of advice I shared was to seek context from the other party involved before making assumptions. As the words left my mouth and lingered in the air, I realized I was doing just the opposite. Here I was offering advice without really understanding the nuances of Jared's situation. I assumed he was asking for guidance and hadn't tried the tactics that I thought might improve the situation.

Jared responded with more context and kindly shared how he tried a few similar tactics in the past. Our meeting was coming to a close, so we wrapped up and moved on.

After the meeting, Joan and I caught up. I was curious to hear her perspective on how I handled the discussion. Sure enough, she observed the same thing I did.

It didn't matter how good my intentions were. By not getting curious, my advice came off as if I knew better than Jared and implied that he was doing something wrong. Not the case! I could see that my approach was making Jared somewhat defensive and resistant.

Albeit a short interaction, it was a powerful reminder to lead with curiosity. When I think I can help someone navigate a situation, it doesn't matter how strong our relationship is. It is critical to ask questions and dig deeper before offering any insight. Gathering context will not only show a desire to learn and understand, but it will also make the conversation that much more productive by being better informed by the other person's reality.

My friend, Sara, reshared this post from Adam Grant on LinkedIn yesterday, and it resonated quite a bit. As I progress in different areas of my life, I find that growth is as much about learning as it is about unlearning.

When we enter the world as babies, we are a blank canvas. We soak in everything and can pick up just about anything over time. We are not afraid until we have an experience that scares us. We feel like we can conquer the world until someone tells us otherwise, or we suffer pain, or we hit a roadblock.

For better or worse, these experiences shape us, the way we see ourselves and the world.

Grant refers to unlearning as having the integrity to admit when you were wrong. While I agree, I think it goes deeper. To me, it's having the integrity to question your beliefs about yourself and the world.

I used to set goals, looking for answers on how to make progress. At work and home, I didn't realize how my own beliefs were holding me back. I had to unlearn to move forward.

Some examples that came to mind when I read Grant's post:

I'd imagine what it would like to be fit, but for years, I'd steer clear of exercise, thinking, "I'm the music and art kid. I'm not supposed to be fit. I don't play sports." Then, I went to college and met art kids who went to the gym. It took time to see myself differently, but I've enjoyed exploring fitness ever since. Getting up on stage to compete in powerlifting competitions meant so much to me because it was so far out of what I thought possible for myself. Funny enough, most of my powerlifting crew was in a creative field.

I think back to years of complaining about stomach aches, searching for answers. Meanwhile, I believed that a meal wasn't a meal without meat. Eating a plant-based diet seemed absurd, so I never entertained it. When I learned about the impact of constant meat consumption, I decided to experiment with cooking plant-based proteins like tofu and seitan. I found that I not only enjoy eating plant-based meals but guess what? No stomach aches.

This week, I started reading Grant's book Think Again which dives further into this concept. I'm enjoying it so far and look forward to continue practicing how to unlearn.