My career evolution

As I looked over the past 25 years of my career, I observed that there were four main types of work I was doing, and their proportions had evolved over the years: learning, doing, managing, and leading.

Learning

In my very first full-time job after college, especially in the early going, I was learning far more than anything else. I was lucky to join a company with an amazing training program – a six-week “boot camp” starting on Day One! – and that set the tone for the early part of my career. To the company’s credit, it took learning very seriously, and I can’t even imagine how much money they spent to train us all for six straight weeks before we ever sat down at a desk.

Once I had completed the boot camp and started working, my learning was far from complete. I estimate that I was still learning about three times as much as I was actually producing (“doing”). Some of the learning was explicit, like more training on a software system or a business process, while other types looked more like an apprenticeship.

If you’re in your early 20s, you will probably not feel this way in the moment, but there will probably be a time when you look back on your early career and judge it not based on how much money you made, but on what you learned, what kind of growth opportunities you got, and the habits that you picked up for the rest of your career. What you learn at that point in your career can set you up for success over the next few decades, often in ways you can’t see until you’re far down the road.

To be clear, this is not an argument for taking on an unpaid internship or letting anyone take advantage of you in the name of “learning,” but keep the long game in mind. You probably have at least 40 years of work still ahead of you, so try to be as deliberate as you can about learning new things!

Doing

As I started to get the hang of things and needed less direction on typical tasks, I started doing the work more. By my late 20s, I estimate that I was doing the work about 50% of the time, and most of the rest of my time was still spent on learning.

Once your career is up and running, the learning becomes more and more “on the job,” in the flow of your team’s normal activities. Once I had demonstrated basic proficiency in certain areas – such as building an analysis model or making a presentation to management – my managers started to include me in more things.

If there was a big meeting happening, in my early 20s, I probably wasn’t even in the room. By my mid- or late 20s, my managers were more likely to say, “Scott, you should sit in on this meeting.” Even if I was a mere fly on the wall, I was learning thanks to the exposure.

Back to the doing: At this stage of your career journey, you’re producing a lot. You’ve become the master of a small domain, and people start to turn to you to get that thing done. Often your reputation grows, and more people seek you out to do that thing, and then one day someone will ask you to start teaching others how to do it.

Managing

I was in my late 20s when I was first asked to start training others. I didn’t become anyone’s direct manager right away, but I started to teach others what I knew and look for ways to help the company outside of my own team.

Once I did get my first direct report, I quickly learned that their success and failure largely depended on me, and it was my responsibility to make sure that they succeeded. At this point, I realized that being the expert on something wasn’t nearly as valuable to the company as making sure my small team could do what needed to be done.

A lot of fantastic individual contributors struggle with making this jump – they’re good at something, so then they’re put in charge of that thing and start leading people, and they hire or inherit people who may not yet be as good at that thing. When faced with this challenge, a lot of young managers will fall back on “I’ll just do it myself,” but that stunts growth for everyone involved.

This tends to be the hardest jump for anyone in their career because they have to unlearn so many habits and replace them with new ones. Is the team confused? Time to figure out a new process and new means of communicating. Is one worker falling behind? Get with that person and understand if they’re lacking the skills or commitment to succeed. Diving in and doing it yourself should be a last resort. Avoid over-functioning, as our CFO Michele Patrick says.

This tough transition is one reason why most companies deal with some amount of the Peter Principle – stars get promoted, but at some point, they’re being asked to do something very different from what made them stars. We think about this a lot at Hennessey Digital when we talk to our team members about their possible career paths – making the jump to the next level will always require team members to learn new things!

Leading

Today, I spend more time leading than managing people directly.

So what is the difference between managing and leading? Managing a team is focused on a lot of the “what” of the work – measuring progress toward goals, communicating with stakeholders across the company, fixing inefficiencies, and finding new ways to get things done.

Leadership defines a lot of the “why” and “how” for the team – Why do we do the work we do? How are we going to grow? Why is our culture important? How do we interact with each other, our clients, and our partners?

Managers most often directly influence their own teams, while leaders usually influence and motivate people across the organization. And this isn’t a strict “either/or” thing – lots of managers demonstrate leadership by bringing out the best in their people, and by inspiring others to take action even if those people don’t report to the manager. And every leader in a company spends some time managing their people’s work.

What has the change from managing to leading looked like for me? Whereas 10 years ago I would often say, “Here, do it this way,” I now come into conversations with Hennessey Digital team members armed with questions and prepared to do a lot of listening. The ideal outcome is when I can help my people arrive at the best way to tackle a challenge or opportunity, mostly on their own.

Don’t ever stop learning

Note that, in the above chart, “Learning” hasn’t gone down to zero. Even the CEO of a Fortune 500 company needs to keep learning and growing because they’re constantly faced with new challenges and opportunities. Career evolution never stops!

A couple of years ago, Jason Hennessey and I started working with an executive coach, Cameron Herold. The best thing about a good executive coach is that it’s rare to encounter a challenge that the coach hasn’t also gone through. Our coach has tackled big challenges, made mistakes, avoided other ones, and has basically “seen it all and done it all.”

Talking through a challenge with Cameron usually helps us see that it’s not as daunting as we thought. He also sometimes talks us down when we fall in love with one of our ideas too much. A great coach helps smooth out the highs and lows of running a business.

Jason and I also belong to Vistage, a peer group for people running businesses in all kinds of industries. Jason belongs to one Vistage group and I belong to another, and we frequently come back from our monthly meetings with great ideas on how to overcome a challenge or pursue a new opportunity.

Where to go from here?

When I close my eyes and try to imagine what my own “Learning – Doing – Managing – Leading” chart will look like in another 10 years, I think the evolution of a career will look fairly similar to how it looks now. For my part, I’m committed to always improving as a leader and finding ways to grow the people on the Hennessey Digital team. I’ve worked for some great companies with terrific cultures and caring leaders, and I love paying it forward!

The post The Evolution of a Career, From an Individual Contributor to a Leader appeared first on Hennessey Digital.

Here at Hennessey Digital, a fully-remote digital marketing agency, we take great pride in continuous improvement in our work and in ourselves. But how can we do that in a 100% remote work world?

The team, the moment, and the space are all here; now the magic of crafting a traditional digital or “tradigital” community that stands the test of time begins…

Value Authenticity

Authenticity in leadership is mission-critical. As we further integrate our digital work and home lives, showing up as our full, true selves lends itself to trust and as a result, commitment, connection, and productivity. Work is not only a place where we meet deadlines, it’s how we spend most of our life.

Inevitably, our connection with our teammates feeds into conversations outside of work hours and enters our thoughts during the most random times. When we can foster our full being and support authenticity without fear of stereotypes is where empowerment thrives.

Encourage showing up in all the ways without fear. A teammate may worry, “If I’m too upbeat, I may be seen as unrealistic, versus as a discerning strategist.” In this example, we must remember that two things can be true at once.

Employ Quality Listening

Quality listening starts by “walking the halls” in this remote work world. “Boots on the ground”-type individuals often make the best leaders, but virtual work has turned traditional leadership on its head.

Endless perspectives, connections, and building of bonding beliefs can be found anywhere. Speak directly with as many team members as you can, including your direct reports, superiors, and team members outside your direct sphere.

Actively acknowledging bids for attention builds strong teams. Everyone wants to be seen and heard. Take the time to proactively strengthen your perception awareness and book time to meet with team members across your organization.

Taking the time to listen and acknowledge your team member’s bids for attention lends itself to situational leadership.

What’s most inspiring and illuminating for one team member may have the opposite effect on another. This is why quality listening through acknowledging bids for attention is essential, particularly for a global remote company.

Me with Jason Hennessey and Jill Wenk at our December 2021 leaders’ retreat at Hennessey Studios

Maintain Curiosity

Curiosity is the cure. As Rumi said, “Sell your cleverness and buy bewilderment.” There are no bad ideas in brainstorming. In this stage, the importance of saying yes vs. no is to keep ideas percolating.

The word “no” shuts down the creative process in the brain and the best idea may not even be “on the board” yet. Cultivating this sense of wonder also makes work feel like play again. Good brainstorming sessions should truly be feel-good sessions; the time for weighing decisions comes later during a strategic stage.

Encouraging ongoing learning is also critical to maintaining a culture of innovation and curiosity, which is why we invest in and follow trends in learning and development at Hennessey Digital. We proudly invest in continuing education for our team, as the Finance team thrived together at a continuing education conference this past summer.

Avoid Over-Functioning

“Over-functioning” refers to consistently executing rather than consistently coaching. Avoid over-functioning as a leader because this enables under-functioning in your team.

As a leader, your goal is to engage your team so that they can elevate their own skills. Asking questions before giving answers or directives is a proven way to create long term skill growth.

Asking “What do you think is important here?”, “What do you think is possible here?” and “How would you approach this task?” are a few intentional frameworks to inspire critical and strategic thinking on even the smallest of decisions.

Coach Your Team Through Mistakes

Coaching people through their mistakes is powerful. Accountability can feel like an attack when a team member may not be equipped to own their own role and appropriately pivot.

This is why it is important as a leader to cultivate honesty and without fear of owning their mistakes. This way, at least there will be a takeaway in creating a solution for future-proofing.

Learning through the sensory pain of a mistake already stings. As they say, “a minute of pain lasts longer than an hour of glory.” During a hard day, remember to encourage the concept that it’s just a tough error, not a terrible performance, so you can grow through the mistake together.

Propose Timelines

Leaving project timelines open-ended could amplify needless worry and divert productivity on other important tasks. And similar to how water takes the shape of any container it’s in, Parkinson’s Law stipulates that work expands to fill the time available for its completion.

It’s tick-tock (not TikTok) on timelines for teams. When delegating to team members, always propose specific time parameters on projects, especially new or ad hoc projects. In support of this, research has shown providing tighter timelines, with perfectionist slack, increases throughput.

A simple statement such as “spend about two hours or less on this and let’s review it next Tuesday” gives information on the level of priority on the project and how detailed the deliverable should be.

Mitigate Unforced Errors

Prove yourself wrong before putting a stake in the ground. We do this to mitigate any unforced errors on our part, not to say an idea shouldn’t be implemented.

It’s important to always ask yourself, “What are we missing? and “What if we’re wrong?” so the team can adjust and iterate on an idea. This is the strategic stage that follows the brainstorming stage, and it’s an important long game skill to encourage in your team.

If you further entrench yourself in your own opinions by trying to only prove yourself right, this often leads to short-sighted outcomes. Janet Yellen, the first woman treasury secretary, goes by this as well, steadfast in her belief that the ability to build consensus around these two questions is critical.

Lay Your Cards on the Table

Allow people in to improve on your own growth goals as a leader. Be transparent in what you as a leader are improving on within yourself and your work.

Vulnerability and awareness of our own areas of improvement build towards the concept of a “we” rather than “you vs me.” It highlights that we are equally invested in improvement and it’s not a top down one way directive.

As the African proverb says, “If you want to go fast, go alone. If you want to go far, go together.” It could be said that creating a functioning global remote team isn’t sustainable, but we’ve been proving that wrong at Hennessey Digital since 2015.

Take these core traditional leadership skills and consistently foster them in your team to craft a strong culture in a virtual work environment that stands the test of time.

(And the cover image for this post is of me, CFO Michele Patrick, Senior Director of People Success Jill Wenk, and Senior Director of Marketing Cindy Kerber Spellman. Because we’ve intentionally cultivated “tradigital” leadership consistently, we love getting together in person whenever we can, like we did in St. Louis for dinner!)

The post “Tradigital” Leadership: Why Collaboration and Inspiration Matter More in a Remote Work World appeared first on Hennessey Digital.

“We should probably include all categories so we’re sure we don’t miss anything.”

“But if we do that, the menu will be too unwieldy and hard for users to find what they’re looking for.”

“We should study all of the other prominent sites in the space and see what categories they have.”

“We can do that, but this client is unique so I’m not sure that those examples will directly apply.”

“Can we just start with a few categories, and then monitor how people are using the site search? If something gets popular, we can add it to the site.”

“Yeah, but while we’re looking at that, the client might miss out on a lot of valuable conversions. I also worry that the bounce rate will be too high if we don’t immediately show people what they want.”

“This is a tough call.”

Decision making and the perfection trap

The menu debate went on for 10 minutes (and I’ll admit I was guilty of prolonging it!)

There was no single “right” answer, and until we had actual data, it was just a battle of opinions.

Finally, someone asked one of our developers, “After we launch, how hard will it be to change the nav and add or remove options?”

“Easy. It’ll take less than 10 minutes.”

Once it became apparent to the whole team that this was not a life-or-death decision and could easily be changed within minutes, it freed us up to make our best guess and move on.

Our decision didn’t necessarily need to be perfect, it just needed to be made.

As the famous quote from General George Patton goes, “A good plan violently executed now is better than a perfect plan next week.”

The phenomenon of decisions

Jeff Bezos touched on the phenomenon of decisions in Amazon’s 2016 letter to shareholders:

Some decisions are consequential and irreversible or nearly irreversible – one-way doors – and these decisions must be made methodically, carefully, slowly, with great deliberation and consultation. If you walk through and don’t like what you see on the other side, you can’t get back to where you were before. We can call these Type 1 decisions. But most decisions aren’t like that – they are changeable, reversible – they’re two-way doors. 

If you’ve made a suboptimal Type 2 decision, you don’t have to live with the consequences for that long. You can reopen the door and go back through. Type 2 decisions can and should be made quickly by high judgment individuals or small groups.

In that internal meeting about the menu navigation, we had been treating a decision about a client’s website as an irreversible “one-way door” when it was a simple choice that could easily be changed.

We had brought out the heavy-duty Type 1 decision-making machinery when all we really needed was a lighter-duty Type 2 approach.

Type 1 and Type 2 decisions

As I looked around our agency, I started to notice other instances where we were taking relatively easy decisions and fretting over them as if they were one-way doors.

And it seems like we’re not alone.

Bezos touched on this phenomenon in his shareholder letter:

As organizations get larger, there seems to be a tendency to use the heavyweight Type 1 decision-making process on most decisions, including many Type 2 decisions. The end result of this is slowness, unthoughtful risk aversion, failure to experiment sufficiently, and consequently diminished invention. We’ll have to figure out how to fight that tendency.

The reality is that most decisions at Hennessey Digital aren’t life-or-death decisions where there’s no turning back. Most decisions we make are Type 2 decisions that:

• Are relatively small in scope (affecting only one project or a single client)
• Can be easily reversed in the future (after we receive more information and realize the original decision wasn’t optimal)
• Benefit from a decision made quickly (taking action on a “good enough” solution today is better than coming up with the perfect solution weeks later)
• Don’t need senior leadership’s input, but rather should be made by managers and those closest to the day-to-day action.

Type 2 decisions can easily be reversed

Some Type 2 decisions are even made knowing there’s a good chance you’ll change them later. A great example of this phenomenon is conversion rate optimization.

When we launch a new paid campaign for a client, we may create a few versions of a landing page to test. Once we’ve collected enough data, we revisit, review, and make improvements to the page based on what we’ve learned.

This process is far superior to agonizing over the “perfect” landing page. Go with what you believe is best, then make adjustments based on what the data tells you.

Type 1 decisions? Those are the biggies; the ones you should spend a lot of time on.

In any organization, Type 1 decisions:

• Can’t easily be undone
• Benefit from gathering as much information as possible, even if it takes more time
• Require lots of time and attention from senior leadership
• Go over better when an established methodology is followed

Think of the kinds of huge announcements that a company seldom makes—merging with a competitor, canceling a product line, or making an investment that doubles the company’s current budget. For these decisions, slowing down and getting it right is crucial.

Getting the Type 1 decisions right

At Hennessey Digital, we make these kinds of Type 1 decisions, but certainly not every week.

Thinking back to early this year, I can think of one big strategic bet that we spent a lot of time on because we wanted to nail it.

This was the decision to move forward with the Hennessey Digital Platform, which is now where most of our client work and communications take place.

As we approached this decision, we:

• Gathered all of the necessary information
• Sketched out a couple of realistic scenarios for each possible path forward
• Brought together the right leaders who were most directly involved
• Picked apart the scenarios, respectfully challenging assumptions
• Finally agreed on a way forward

Two things about this decision stand out to me now.

First, it took a long while; much longer than we want most decisions to take. The time from when the idea was first floated to when we made the decision to move forward was over two months.

While we probably could have met more frequently and decided sooner, this realistically was going to be a months-long decision because of the fact-finding work that had to be done. (Remember: we’re okay with this for the big decisions.)

This highlights another key factor in both Type 1 and type 2 decisions: info-gathering and missing data.

How much information do I need?

The second thing that stood out was that, despite all the fact-finding and time spent carefully weighing everything, we still had less information that we would have liked to have.

Well, what do you know? Jeff Bezos wrote about this, too:

Most decisions should probably be made with somewhere around 70 percent of the information you wish you had,” Bezos wrote in the letter. “If you wait for 90 percent, in most cases, you’re probably being slow.

Don’t get too hung up on that 70% number. I don’t know if it’s really more like 60% or 85%, and that’s not the point.

You might have enough experience and the managerial judgment to know that there may be significant unanswered questions. But we have the information to generally know what we’re dealing with and what the most likely outcomes are.

This was the situation we found ourselves in earlier this year. While I personally still had a little nagging voice in the back of my head asking, “What if we could talk to a few more people and learn a little more?”

I knew it was time for us to move forward.

Involve the team in decision making

For day-to-day decisions that our agency makes all the time, we’re making an effort to let managers and individual contributors make more of these decisions on their own. Some decisions should be free from senior management’s input and not involve weeks of digging for alternatives and chasing down obscure “what if?” scenarios.

If we make a decision that needs to be revisited, that’s okay. We won’t bat 1.000, nor should we. (And this is where the principles of Type 1 and Type 2 decisions come into play.)

Don’t obsess over getting every decision right. And don’t stress over some occasional misfires: those come with the territory as we push ourselves to move more quickly with our decision making.

Hemming and hawing for weeks to make a slightly better decision isn’t how Amazon got to where it is today. Hennessey Digital isn’t Amazon, but we want to embrace this philosophy more and more as we grow.

As Franklin D. Roosevelt once said, “It is common sense to take a method and try it: If it fails, admit it frankly and try another. But above all, try something.”

And that’s what we do at Hennessey Digital!

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We scoured the talent pool, interviewed several candidates, identified our top choice, and made an offer. The candidate gave us every indication they would accept, and we waited for them to respond.

We waited, we waited some more, and the candidate finally got back to us. They turned us down, saying they were going another direction with their job search.

What happened?

Getting rejected felt like a kick in the gut, but it was something we needed to hear.

Every company thinks it’s the best place to work, has the best people, and offers the best benefits to employees. But as we’ve learned, you have to constantly keep your finger on the pulse of what’s happening in the market and within your own organization to be able to find and keep the people who will move your organization forward.

Getting Honest With Ourselves

Losing out on this key potential hire for our SEO team was a hard pill to swallow, but it’s a lesson we needed to learn. As a growing organization, how can we attract and retain top talent to achieve our goals for growth and success?

We needed to look at how we were doing things around here and find ways to improve so we wouldn’t have another strong candidate turn us down again. Our founder and CEO Jason Hennessey turned to his executive coach, Cameron Herold, for guidance.

The initial feedback that Cameron gave was that “your talent magnet wasn’t strong enough.” But when Jason told Cameron that we offered only two weeks of paid time off to employees, Cameron was aghast.

“He actually closed his laptop and said he wouldn’t let his son work for us, our PTO policy was that bad,” Jason shares. “It was time to get honest with ourselves about how we were doing things.”

Soon after this conversation, we increased our PTO from two weeks to three weeks, and team members start to accrue PTO at a rate of four weeks annually on their one-year anniversary (or “Henniversary”, as we call it). This PTO benefit is on top of paid sick leave, which we also recently increased from three days to five days annually at the beginning of 2021.

We also added bereavement leave to our benefits offerings, which was another way of taking care of our team members that aligns with our culture at Hennessey Digital. More on that later in this post!

Don’t Wait to Make a Change

As soon as losing out on this key potential candidate happened, Jason and the Executive team knew they wanted to strengthen our Human Resources efforts. We recruited Greg Herrmann, our Senior Manager of Learning and Development (L&D), and Jill Wenk, our new Director of People Success. Immediately, we saw positive effects of their joining the team.

Right away, Jill and Greg added value with their respective skills and experience. Although it’s unusual for an organization our size to have a dedicated L&D person on staff, we knew that we wanted to emphasize training and career development for our team members. We have a strong culture of learning and innovation, and adding Greg to our People Success team was an investment in this strategy. Together, Jill and Greg reviewed each procedure and policy we had and introduced fun, creative, supportive solutions for our team members.

At Hennessey Digital, our focus is on taking care of the team, because they take care of the business.

In February 2021, several of our team members in Texas were affected by the snow and ice storms that left them without power and water for days. Our Executive and People Success teams acted fast, quickly adding a “Natural Disaster” paid time classification so these team members could be paid for this time without having to use PTO they had accrued.

With each of these initiatives, a need presented itself and we acted fast. We value our ability to take action quickly if the situation warrants it, and this is a critical component of the culture we’re continuing to build upon at Hennessey Digital.

Join the Culture Club

The phrase “work culture” can mean different things to different people and organizations. To be successful, we must be a company that people want to join and stay at for a long time. We need the right people in the right roles, moving together in the right direction. But how do we make this happen?

“Culture” means several things to us as a company. It means the language we use with each other—including inside jokes and phrases that only a member of our team would understand—and how we treat each other. It also refers to our goals and strategies (how we do business), who we work with (and who we don’t), and our values and expectations.

Our founder and CEO Jason Hennessey frequently talks about how important work culture and leadership in a remote world are. Years ago, he sent an unsolicited email to Zappos CEO Tony Hseih (rest in peace) and was invited to tour the Zappos headquarters in Las Vegas. This experience made a strong impression on Jason, and he learned that culture is invaluable when you’re building a business.

In late 2020, we initiated a project to create our core company messaging. This process involved clarifying our vision with the executive team, gathering feedback and input from our functional department leaders, and collaborating to create and finalize our mission, vision, core values, and unique value proposition.

In creating our core messaging, it was critically important to us to make sure we didn’t translate one person or one department’s idea for what our organization “could” or “should” be. We needed to translate the strong culture that we already had into words, and we came away with messaging to support our business well into the future.

Measure Your Progress

In the fall of 2020, we conducted our first employee survey to determine our internal net promoter score or NPS. This was our first real effort to quantify how satisfied our employees were with us as a company, and we earned a score of 71.2. It’s a respectable score, especially for a first effort as a world-class score for NPS is 80. But we knew there was room to improve as we worked to fulfil our vision to become the undisputed legal marketing leaders while building on our reputation to grow into new verticals and services as the best place to work in the industry.

After this initial net promoter score calculation, we made changes at Hennessey Digital. We upgraded technologies, made enhancements to our team member benefits, and hired key people who continue to improve our systems and processes so that we can deliver excellence to our clients. In March 2021, we conducted our second internal employee survey and earned a net promoter score of 77.6. A great score, and also a great opportunity to improve even more!

At Hennessey Digital, we believe that measuring employee satisfaction is one way to empower our people and communicate that they are valued. Our CFO Michele Patrick says it best: “We want to empower our people to find what lights them up inside and allow them to do more of those things by continuing to incorporate autonomy, flexibility in their schedule, and opportunities to grow and reinvent themselves. There is always time for curiosity and expansion, and that power is truly in every one of us.”

When we hired our Senior Director of Marketing Cindy Kerber Spellman in March of 2021, she shared with us that she’d received multiple job offers on the same day: from us, and from two other organizations, one of which has a recognizable name and high company profile. Cindy accepted our offer, and she shared with us that our people and our culture are what sealed the deal for her—high praise and a clear sign that we’re doing something right!

Lessons Learned

We lost out on a key potential hire last year, and since then, we’ve learned things about ourselves that have helped us grow and get better in areas we needed to improve.

We’ve learned some important lessons along the way, and here are our top tips for enhancing your work culture and positioning your organization as an employer of choice:

Keep things fresh

Just as your business strategy and goals require periodic review and updating, so will your policies and procedures on how you take care of your employees. What’s considered “new” or “market-competitive” changes constantly, so you need to review the benefits and perks you offer regularly to keep your talent magnet strong.

If it matters, measure it

It’s not enough to simply say “we want to improve x, y, and z”: you have to be willing to put in the work to measure what’s important to your organization. Without meaningful metrics in place, it’s impossible to know if you’re improving from one measurement period to the next—and by how much.

The work never stops

When it comes to company culture, it’s a marathon, not a sprint. Learning and innovation are cornerstones of how we do things at Hennessey Digital, so we know that there’s no “there” or destination we’re going to arrive at, but we have our core principles and the 127 Code of Honor to guide us. We constantly work at improving our culture, what we deliver to clients, and our talent magnet to attract and keep the best people in the industry for our team.

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