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I build IT teams and tech for early stage companies. I recognized the same challenges at each startup, so I set out to create a set of standards for early stage companies navigating the tech ecosystem. Learn more about my philosophy or inquire about engagements at The IT Plan.

Over the past 10 years, I’ve been s-l-o-w-l-y making the change from a high-performing individual contributor or HPIC for short, to a Technical Manager. If you’re in the same boat or considering the transition, you may be wondering when someone is going to take you aside and say, “psstt — here’s how you do it”.

The truth is that a large part of this transition will be personal work that falls to you.

And it all starts with conscious acknowledgment that the ‘stumble through the dark’ is best avoided. Mentorship and leadership trainings, non-technical certifications, self-study and reflection, enrollment in a Master’s degree program, even YouTube videos are all real pathways available to you.

Do not let it feel like something that’s just happening to you. Take the reigns to LEVEL UP for this next stage in your career.

While we’ve all had managers, they may not have been appropriate examples — let’s baseline for a moment.

What separates the dreamers from the doers is action, but good news — you’re already on your way.

The tools, habits, and traits that have you’ve gotten you this far in your career are excellent for developing the next stage of it; but in order to succeed, you will need to identify and adopt new tools. What you’ll find below are shortcuts from my personal experience, developed in the IT field, but conceptually applicable to all.

This is an important journey in your career and will change how you view success and work. Let’s get started!

What again, is a Technical Manager?

A technical manager is the multi-tool of career positions. They are project managers, artists, negotiators, and therapists. As a project manager, they identify, justify, and schedule work to improve the output of the business. As a therapist, they are foremost empathetic to the needs of others but as a negotiator, they confidently achieve consensus between technical and non-technical department requirements. Much like an artist, they take every opportunity to highlight their team’s hard work through engaging visuals and storytelling.

The world sorely needs good technical managers, so let’s take the first step because, well, we need you.

Change The Way You Think

Transitioning from a hands-on, technical role into a strategic position will be the most challenging task in your career. It requires a entirely new way of seeing work.

Let’s be honest— you’ve become a high-performing individual contributor because of your ability to:

1. do the work (productivity), or,
2. champion a solution/be the subject matter expert (SME) (knowledge), or,
3. stay hyper-focused on developing your skillset (interest-driven dedication).

But success as a manager will be defined by your ability to:

1. Achieve outcomes without performing the work (delegation), and,
2. Learn how to develop another human being (empathize), and,
3. Elevate your perspective (Big-Picture Thinking), and,
4. Function inter-departmentally (Socialize/Compromise).

Take notice of how the ‘ors’ become ‘ands’. Looking after people and processes comes with more checkboxes and responsibility than managing technology.

We’ll learn how to change the way we think by:

• identifying alternative paths to achieve outcome,
• learning how to ask the right questions,
• developing a management style,
• garnering support for our ideas,
• zooming out to see the big picture,
• learning where to look for great talent.

Let’s look at how success as a manager differs from success as an HPIC.

Achieving Outcomes

‘Doing the work’ and delegation are different approaches to the same outcome.

To date, you have excelled by executing a solution. We need a domain? No problem — setup some AD controllers. We need 802.1x? No sweat, you knew this was coming and added the NPS role to the server, utilizing RADIUS for authentication to the corporate WiFi network— what’s next?

As a manager in this example, your success no longer depends on your ability to execute this project, rather, it will shift to guiding or training a direct report to identify solutions and plan the project.

While you’re ultimately still on the hook for a successful outcome, you can’t achieve it by doing the work yourself. Sherpas do not take people to the peak by carrying them.

To practice, we can try an exercise — do you practice yoga? In the Western world, we equate yoga with asana or, holding poses but this exercise is accessible to all.

Exercise: Using only your words, guide me from standing into a forward fold. No touching, no demonstrating — tell me how to move my body to achieve the outcome you want.

Did you start by telling me to bend over? Where, at my knees? Oh, my hips. Okay <proceeds to dump body in a forward motion, achieving a 10% bend>. Now what?

As with any mountain clumb, there are many paths that you can take, let’s look at one of the many answers to this exercise.

1. Stand up straight with your feet together, hands at your sides.
2. Relax your shoulders, chin up, stick your chest out.
3. Engage your abs to lift up out of your hips.
4. Stick your butt out and slowly bend forward at the hip.

Now, I want you to internalize some things.

First, some paths might be better than others (more efficient/less taxing), but there is no single correct/right path and we often find the better one in hindsight (which is why continuous improvement is so important).

Second, and most important, —

Knowing how to do something isn’t the same as telling someone how to do it.

In a nutshell, this is delegation and learning to do it properly will ensure you become a multiplier of successful projects and outcomes.

Permit Questions To Become Your Answer

The ability to execute a task is entirely different from directing execution of a task.

A key to successfully scaling and sustaining productivity is to become a multiplier. Julie Zhou’s book, The Making of a Manager, can be considered required reading on the topic.

Let’s take an example of building a server. As an HPIC, you know how to build a server, but as a manager, your direct reports may not have the experience and you will need to guide them without doing it for them. You can achieve this by asking questions such as:

1. If I were not here, where could you find that information? (Discover)
2. What do you think would be some good first steps? (Empower/Plan)
3. How would you recommend we break down the work into manageable chunks? (Plan/Action)
4. So, where do you think we should go from here? (COMBO MOVE)

You’ll notice that most of these questions are designed for your report to lead the conversation. While you can provide the direction by just telling them how to make the server, you’ll ultimately set everyone up for success by helping them equip their own toolset for future projects.

In the story of management, you play the role of guide, not hero.

Scenario: Without a centralized authentication authority, staff are logging into desktops with local accounts. You know that Active Directory is an extensible architecture that expands into Microsoft’s Azure AD for a hybrid cloud deployment. This solution would anticipate the company’s shft towards a SaaS based, cloud environment. In your weekly 1:1 with a Systems Engineer, you may ask, “Hey — what do you think we should do about all of the local computer logins?” and they say “At my previous job, everyone had an active directory account to login to their computers.” So you say “That sounds like a good idea, do you think that would be a good fit for us, too?”

In this scenario, you’re beginning to shape strategic outcomes without executing the work yourself.

Again, no single path is the correct one and your may have direct reports who become frustrated or disheartened by your use of the Socratic Method. In order to avoid this, you’ll need to learn when to offer support and when to hang back and listen. The unique application of these tools will shape your management style.

Develop Your Management Style

Not all of your reports will need the same degree to direction. Identifing and adapting your management style to the preference of your reports will be required.

In his book, The Laws of Human Nature, Robert Greene outlines many strategies to navigate a variety of human interactions. His insights can be employed generically to provide recommendations and make requests of others. With this insight, you will come to recognize certain dynamics in your relationships in all direction — laterally, downwards, and upwards.

When you understand human nature, you can start to explore managerial frameworks such as servant leadership, visionary, or transactional styles.

The particulars of your adopted framework will be influenced by what has worked for you in the past and must be a reflection of the feedback you’ve received as an IC. Have you been told you are a strong leader or highly demoncratic? Do people tend to follow your lead or are you a great facilitator of outcomes through group discussion and debate? Some of your characteristics should be reinforced while others may need to be balanced.

While the style you choose is up to you, there are certain components of management you must learn to adopt. They are:

1. Understanding the role of HR
2. Inclusion
3. Systems of rewards, accountability, and responsibility

As a personal example, I have a high degree of conviction in my determinations and often trust my sense of direction without being able to fully articulate the origin of it.

Early in my career, I would aggressively attack every problem with a solution but was once under the direction of a manager who preferred a ‘wait and see’ approach. Whenever there was a potential issue, I would offer up plans and he would often respond by saying “Let’s wait and come back to this in a few days.”

And it would drive me crazy!

It felt foolish to let problems exist in what could be a well-oiled network machine. Over time, as I witnessed problems disappear entirely or be resolved simultaneously, with no effort, I came to appreciate this perspective and often employ it myself as a manger. Not every problem requires the respect of a dedicated solution. Deciding when/where to pay attention or expend effort is a characteristic of successful managers.

Soft Skills and Making Decisions

Akin to a doctor developing their bedside manner, IT staff should do the same with their ‘desk-side manner’.

A successful technical expert will train themself to understand problems from a technical perspective — how systems and software interact and communicate (aka Systems Perspective or System Level Thinking).

As your focus shifts to people management, this will be replaced by a need to understand how people use technology. This transition will be reflected in the questions you pose to work through problems:

1. How would I feel if I had this problem?
2. How will this change affect a person’s workflow?
3. What factors are driving my employees’ needs or interests? Ease of use? Functionality?

You can develop this skill through exercises in patience and reflection upon personal experiences. Empathy will influence your decion making processes, as will an ability to identify and understand the differences between urgency and importance.

Your relationship with time will combine with your acute business and technical acumen to unlearn the habit of giving everything equal attention.

This is important. Where your attention goes, energy flows. Your new role will require correctly identifying and separating what is urgent, important, and what is not to direct resources towards high value problems.

Look at the following examples through the lens of an IC and classify them as urgent, important, or both.

• Person A cannot login to email because they forgot their password.
• A firewall issue is preventing an entire office from accessing the internet.
• Your CFO is asking for an updated Q2 IT budget for next week’s team meeting.

Now, look at the examples again through the lens of an IT Manager or Director and classify them as urgent, important, or both. Did your answers change?

Deciding not to pay attention to a particular problem will feel like inaction and feel unnatural to you, but it will become more comfortable as you expand your field of view and problems/issues are re-prioritized.

I hate to be prescriptive, but…

Avoid becoming a reactive decision maker. Working from a reactive state is a short-term mindset and creates a false sense of urgency. The risk of burnout and malaise increases the longer your team operates in a state of urgency and reaction. Instead, operate from a long-term viewpoint and train your thought processes to bring the horizon into focus.

Zooming Out

Much like moving from a first person point of view to that of a third person in a video game, transitioning into a managerial role shifts the focus of your success one level back.

IC’s are often subject matter experts and are accustomed to designing and implementing solutions. An IC operates ‘in the weeds’, while a manager should operate from the sky and only land to visit.

This means that as a manager, you’ll have a wider field of vision, but less depth.

Not to worry — others will fill in for the lost depth — it’s now your responsibility to set the agenda and empower them to enact it. Be aware, if you have trust issues, you might trend towards micro-management. For right now, though, just be aware of it.

In order to develop a high level mindset, you may wish to ask the following questions when approaching initiatives.

1. How do we achieve alignment between our processes and organizational objectives?
2. Which metrics should we monitor to indicate success or identify improvement opportunities?
3. Which silos can we move to consolidate into a unified system?

Generally, these questions are all concerned with effects over a long period of time and adopts the same principles as investing early — small gains will compound and add up to big wins.

To excel, some of the tools you can employ are:

1. Creating a roadmap or strategy that aligns with company OKRs.
2. Identifying major problems and work backwards towards solutions.
3. Creating templates and guides for compounding time-efficiency gains.

The commonality between these tools is planning — and that requires forethought.

Think of it this way…

If you want to go on a hike or go camping, would you just show up to the trailhead one morning?

What are some of the ways you might prepare for a hike? Would you buy a map ahead of time? Plan the route? Pack a lunch? Charge your cell phone? Tell a friend where you are going? Check the weather?

Start to approach your work life like you would a new hike.

Real World Exercise — Prepare an agenda for the next meeting you plan and build this into your schedule so it becomes automatic. Stretch goal — adhere to the agenda and time!

Identifying Talent

Fostering a good culture is partially accomplished through guarding it.

In the process of becoming a manager, nothing has held me back more than knowing when, how, and who to hire.

Learning when or who to hire may be an improvement opportunity for you if you are:

• consistently overworked,
• straddling multiple iniatives and playing multiple roles, or
• never able to prioritize high level thinking.

Even after 10 years of hiring and managing people, I’ve only improved the ‘when’ to hire, but I trend towards hiring junior over senior. It is evident when I have a team of 5, but finding myself identifying and leading all the projects.

This is a difficult lesson to learn through experience and you will save yourself a great deal of anxiety by mastering these concepts with a mentor.

Similarly, learning how to hire will be a baseline skill that all managers must develop. Some key skills that hiring managers will need are:

• Crafting a neutral and inclusive job description (JD),
• Understanding role budgeting, setting appropriate compensation bands, and learning which perk levers are available to offer candidates,
• Identifying candidates on LinkedIn, through your network, and/or by reading their applications to your job posting,
• Creating an interview panel, skills assessment, and scoring rubric,
• Encouraging candidates in offer acceptance and throughout their start.

If you have the benefit of an internal recruitment team, you can lean heavily on them for all of these items. If not, you may be researching and copying what has worked for others until you develop confidence in your assessment capabilities.

Luckily, there are many interview tools that exist to give you a starting point. From experience, I can say that this is an area of management where you will wish to exercise as little creativity as possible. Established pathways for how to structure teams, creating job descriptions, and how to interview and grade candidates exist for a reason and you should have plenty of autonomy as a manager to focus your creative efforts on achieving outcomes.

Guidelines for a Successful Transition

Here are some tips I’ve learned since making the transition to a strategic leadership position in IT.

Mentorship & Reading

Becoming a manager requires accepting responsibility for enabling others to succeed — taking that lightly, or even unknowingly, is setting yourself, and those who report to you, for failure.

Many IT people have learned by tinkering and testing — in short, experiencing. While this is beneficial in figuring out how components of a finite system work together, it spells destruction when managing people.

If I were to chart my own path again, I would certainly include a mentor, but the titles below helped me bound up the steps to developing good management principles.

• The Making of a Manager by Julie Zhou
• The Manager’s Path: A Guide for Tech Leaders Navigating Growth and Change by Camille Fournier
• The First 90 Days by Michael Watkins

Obtain Non-Technical Certifications

If you haven’t already, identify and achieve certifications in project management and service and process management to develop your business acumen.

The skillset needed to succeed as a manager is entirely different from the skillset that helped you succeed as an IC. You’ll no longer be configuring the settings, but instead be developing a budget and timeline, justifying costs, and writing policies. You’ll need to play the politics game and advocate for projects by building consensus across departments and showing the benefits in charts and slide decks.

The following are certifications empowered me to speak the managerial language.

• Certified Associate Project Manager, Project Management Institute (CAPM — the PMP’s little sibling)
• ITIL v4 Foundations
• Yoga 200HR Training

Learn to Inspire

One of my strengths as a manager is facilitating understanding through the use of analogies. I love to engage in philosphical discussions that intersect with business — learn about human development, work/life balance, and motivation techniques. These concepts will supplment leadership strategies and there are a great number of influential figures in this arena.

Naval Ravikant, Simon Sinek, Gary Vaynerchuk.

Stealing from them until you’re able to develop your own perspective on work and life is highly recommended.

Become a Facilitator

As an IC and SME, you’ve learned to help your customers ‘cut to the chase’ and give you the problem so you can design the solution. As a manager, you’ll instinctively want to do the same — hand out solutions to problems.

Prior experience has taught you how to address a problem in the way you would address a problem. Going forward, others will be addressing the problems and telling them how is robbing your reports of their ownership over solutions.

Think of it this way — there are many ways to increase customer satisfation through helpdesk tickets such as implementing SLAs and metric tracking. Some managers will increase resources to address problems, provide additional training to support staff, or add pathways to request support. These are good initiatives but they all lack participation and exercise with your staff to re-establish what it means to support someone. Ask your team this question but refrain from dominating the conversation and you’ll gain some insight that no survey will provide.

Training Opportunity

Ask your team to go out and submit a support case with any external party. Maybe they bought a rotten apple from Whole Foods and want to return it. Maybe a package from Amazon didn’t show up.

In tandem with metrics and SLAs, provide an opportunity to empathize and examine qualitative self-assessment questions. Upon closing a support ticket, ask them to put themselves in the shoes of the person they helped and answer the following questions, “Was someone there when I needed support? Were they knowledgable in their answers and guidance?” If the answer is yes to both questions, it was likely a positive experience. At the end of the day, isn’t that the goal?

Understand Modern Managerial Practices

Research and adopt modern managerial practices. Learn how to write a 30/60/90, format a 90 day review, ask yourself what you want to accomplish through 1:1’s. Challenge the frequency of meetings and their goals to identify the core reasons for their existence. This will not only help you keep focus by reducing noise, but is a critical time management skill.

There is a wealth of knowledge in Harvard Business Review and other sources which has been distilled through innumerable blog posts — free to find through Google. Good managerial practices spread like wildfire — there are no secrets here. However, to be successful, you must combine this with your practical experience which is the best part of the process — learning to lead in your own unique way.

Reach out!

These recommendations are just the tip of the iceberg when it comes to organizational technology postures and IT management practices. Please reach out if you’d like a consultation customized for your business.

If this was useful to you, please consider looking at the follow-up outlining the transition to leadership.