I studied Art History in college and find the liberal arts to be one of the biggest influences in my design career. One of my favorite eras to study is Baroque art. It often brought high contrast, strong asymmetry, aestheticized violence, and remixed symbolism in its works. It’s the Tarantino era of art history. One of the artist who first caught my attention at an early age was Michaelangelo Mersi, better known as Caravaggio.

The Catholic Church at the time were huge patrons of the arts and commissioned artist to create paintings of famous scenes during the counter-reformation. Caravaggio, is what you wouldn’t necessarily call a religious man, which made his works so fascinating to me; an amoral man and sinner in the views of the church, being commissioned by the church. He often left a lot of room for interpretation in his paintings. One of the famous ones is that of “The Calling of St. Matthew”.

The 10.5×11’ oil painting in Rome depicts the moment when Jesus Christ inspires Matthew to follow him and become an apostle. In the painting, it’s not clear which one is St. Matthew. Is it the young man hunched over the coins? What about the main pointing at himself to ask “me?” Art historians have often said Caravaggio left it open ended for the viewer to interpret that the calling can be for anyone.

I use this piece of art not as religious evangelism but perhaps career evangelism. This painting often reminds me of how people get called into management, and how ambiguous it can be where great future managers come from. Perhaps it’s the 10x engineer who points at himself and clearly assumes it’s him. But what if it’s the average senior designer who has a great emotional intelligence (EQ), organized, and really cares about people?

The current state of management

Since it’s what I have the most experience and observation in, the purview I’m going to share is primarily design management, though I believe this applies to many other functions and disciplines as well.

The industry sets up wrong incentives for people to become managers

The candid truth is that there are a lot of managers in positions who shouldn’t be. It’s not to point fingers as they come in many forms and they come in many forms. Perhaps it is someone at an early startup and fell into management as the company grew. Some pursue management positions for personal gains and have more perceived influence. As we ponder who would make good managers, we also must ensure that people who have a desire to thrive as individual contributors and leaders have incentives to do so.

The system often incentivizes people to go into management for the wrong reasons. There’s often a pay bump in becoming a manager. I believe that’s the wrong incentive, but that’s a different blog post.

At Webflow, we have individual contributor (IC) designer tracks that have parity with manager tracks, both in pay and influence. Leadership is a trait both managers and individual contributors have. If we’re going to fix the management pipeline, then we need to ensure individual contributors have clear and equal tracks. Buffer has a great article about their individual contributor career track.

Lack of a succession pipeline and development process

“There is no success without a successor.” — Peter Drucker

The core problem I view is that there is a substantial gap in the management pipeline for new managers. As experienced managers and leaders in the industry retire (and they will at some point) there needs to be a clear investment for new managers to take the mantle.

A lot of managers transition into lateral positions at different companies. Roughly put, the same people are getting the management jobs, and not all of them are good managers. At this state, these managers will continue to fail up if there isn’t any dilution of the talent pool.

While this is happening, some of the best potential managers may be neglected from pursuing management, both by external forces and perhaps themselves. The biggest problem I see is the lack of encouragement from others for them to pursue management. In a land of bad-to-middling managers, sometimes people who would be great managers don’t see themselves in management positions because the people they do have as models aren’t who they want to be.

The industry needs good managers, which is not necessarily managers who have been doing it for a long time. The management pipeline needs to be refreshed from time-to-time with new people to take on the responsibility.

Companies are looking at historical data to de-risk

Hiring is important to get right at a company. Make the right move and you might find the person who is going to shift your team and elevate them. Make the wrong hire and it can be costly and dire. The impact is felt even higher for management and leadership roles. It’s no surprise then that companies are seeking methods to de-risk the hire.

The desire for more “influence”

I’ve often heard in many conversations with people considering management state that they want to pursue it to mentor and have more influence. It’s understandable how people might feel this way, however, it’s not good motivation to enter management. When you are in a higher leadership position, your role is more motivation and coaching than influence.

The calling of ICs

I firmly believe that some of the best new managers are currently individual contributors who have not considered management or shied away from it.

If you would have asked me a decade ago about people managers, I would have laughed. Never would I have imagined taking on a role as an introvert where the majority of the responsibility is dealing with people. My motivation then was to strive to be the best individual designer.

What makes a good manager?

Though this clearly varies based on company and industry, I’ll try to boil it down to the essentials based on experiences I’ve had and observed. At the core, a good manager is someone where their highest impact is focused on developing people, processes, and systems that provide farther value than what they can achieve as an individual. Your focus transitions from heads down to heads up.

Your focus shifts to the success of others

Clearly individual contributors also care about other people, however, the success of others is one of the core performance indicators in management. If you find joy working with people to enable them to be better at their job, management is a great place to do that.

The turning point for me was when I realized that focusing on spending time with other designers to help them get better brought me so much more joy than heads down time to explore a new project or prototyping tool, which I was very much in love with. Seeing where people started and witness their development became what I cared most about.

People-centric approach, team-oriented outcomes

You care about people but your mission is that of the team. The team is your metaphorical product and you’re responsible to strategize, unblock, and scale. Empathy and advocacy for your people is the natural start of being a manager. However, to be a strong manager, you will have to thoughtfully balance the needs between every human and the team.

Enabling people and systems

As a manager, you are now a builder and maintainer of people and systems. The responsibility of a manager is not to be good at everything, but to ensure the team is effective at everything.

The greatest system design challenge in the history of humanity is getting people to work together effectively.

I’m interested. So how do I get in?

If I’ve peaked your interest, here are some things to think about to prepare for the calling. The trick is to distribute your impact and influence as you’re a high performer to transition into a higher scale role. There is no shortcut to management. Be sure you’re a consistent and high performer at an IC level. The trick is to convey that your time can be maximized as a force multiplier.

Remember, if you don’t like management, you can always go back to being an IC in your career. There is nothing wrong with that. There are different layers of management, and you don’t have to keep climbing the ladder. Find the purview that gives you the most joy. If you enjoy first-line management, you don’t have to climb all the way up to executive. They have different roles and responsibilities.

Even if you have never thought about it, I encourage you to dip your toe and get some taste of management. You may find it be the calling you never expected.

It’s often said “the best ability is availability.” In order for people to champion your management track, you must make it known to people you’re considering it. This sounds obvious, but crucial. If you never speak up, people might assume you prefer to be an IC. Here are some ways to dip your toe into management.

Start taking on process projects

The hardest gap to fill is to show people you would make a good manager when your resume has only been as an individual contributor. Identify a gap and volunteer to take it on with an action plan. An example of a process project could be a proposal to improve a design review process during critique or drafting a standard operating procedure for the team (SOP). As you take on process and team tasks capture impact metrics on the return on the time invested in you working on such things.

Advocate for junior people and do it consistently

Note that I didn’t say mentor. If you don’t have any, mentor ones externally. There is no shortage of new designers looking for a great mentor and sponsor.

If you want to get a taste of management, then you have to do it consistently and be involved. Mentorship is great, but it’s a different type of focus. To get a taste of day-to-day management, coach someone more junior for them to take action, follow up and keep track of progress.

If you don’t have junior people on your team or company, work with people externally. I assure you people will be thrilled for the time you offer up.

Prepare for the calling, give yourself time

It’s not too soon to start thinking about a management track in your career. However, give yourself time for the opportunities to form for you. Your career is a marathon, not a sprint. Start prepping for the opportunity and it’s not too soon to commence.

Ask the question and perhaps answer the call

What does your heart and intuition tell you? If you sense a signal, dip your toe into management. Reach out to leaders to get their advice. If you’re interested in talking about it I’m happy to discuss personally or connect you with an advocate.

Remember, you don’t have to make a decision right away, though I encourage you to start exploring those capabilities. Accrue evidence as you begin the management dialog.

Take a moment and ask yourself, “What if the future cohort of great managers and leaders includes me?”

Notes

Special thanks to Julia Ferraioli for editing.

If you ever want to discuss management, shoot me an email and I’d be happy to discuss with you or connect you with another experienced manager.

Sources Cited

• http://www.visual-arts-cork.com/famous-paintings/calling-of-saint-matthew.htm
• https://www.mentalfloss.com/article/67050/15-things-you-should-know-about-caravaggios-calling-st-matthew

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