johnpfeiffer

Front Line Manager or Director - Managing People Managers

Titles mean nothing

People get hung up on titles and status: "Manager"... of what? Does this mean you get to tell people what to do? So a Director directs people?

The job is always to solve (hard) problems and create value.

The kernel of truth: Manager and Director are distinct in expected outcomes and focus areas. Director is not as simple as Manager++ or VPE--

A front-line manager's focus is the immediate results and to care about people who do the work.

A director's focus is often upward and outward: outcomes that matter to the organization and business, teams and systems that accomplish those things.

Managers are necessary overhead

Why aren't top sports teams "self-managed"? These top athletes are the best at what they do, so why do they have a coach?

People want consistently winning teams.

If the CEO could just directly tell everyone "Do X" and it worked, they would.

Likewise every Individual Contributor would prefer autonomy and to focus on their work rather than having to "report to someone" and "performance evaluations".

A manager represents stability for an organization: a continuing business function that has clear ownership. A dependable and reliable part of the larger structure.

A manager is not "the next rung up the ladder" for an IC but a completely different kind of work, requiring unique skills and responsibilities.

It is a lateral move into a different discipline like Design or Science where prior skills and experience don't transfer automatically.

Good managers are worth their weight in gold - or even their weight in bitcoin ;)

Creating leverage is valuable

What does leverage look like as a People Manager?

An engineering IC creates a frequently used software library or widely adopted architectural pattern: "leverage" to multiply their impact on the organization (and beyond).

A people manager can uniquely scale their effectiveness and influence by:

  • hiring and retaining great people
  • converting chaos into an efficient process
  • building a great culture

Every org has a lot of noise, someone needs to filter for signal and help provide emphasis.

As a great manager - manage yourself

As a Great People Manager, you first manage yourself =)

  • Are you self aware of your emotional state and mindset - how are you showing up and connecting to others?
    • Do you bring positive energy to your team and colleagues?
  • Do you know what the highest priority most impactful things that you can do are? Effectively manage your own time and calendar?
    • Have you spent time trying to understand how your manager and company's leadership team communicate? What is their mindset and favored mechanisms of communication?
  • Professionalism: on time, prepared for meetings and conversations? Take notes and have action items? Own your action items and follow through?
  • Do you communicate clearly in writing, verbally, and with images and diagrams?
  • Do you understand your own strength and areas for improvement, what kind of personalities complement your working style?
    • Are you deliberately investing in improving your skills and opportunities for more experience?

What does a Manager even do?

The job is often reminding people of things they already know ;)

The Manager role is indirect and requires patience: long periods of boring (necessary) work punctuated by busy extremes (hiring, performance reviews, promotions, layoffs, receiving resignations)

System/code deep dives are intellectually draining - but often emotionally "neutral". People are not logical software. A people manager's role is integrating humans into a system, and humans are emotionally taxing.

And the job involves common sense: request PTO in advance (so people can cover the work), don't show up 20 minutes late for every meeting.

A manager cares about Results and Retention

A people manager has to "show up", especially in critical times, but overall it is a role requiring reliability.

Quality Control

Increased responsibility means more accountability. Every time you hire or promote someone you are putting your credibility (as a decision maker) on the line.

Having a background in a given domain makes it easier to identify when things are going wrong, or performance issues. (For instance, modifying code directly in live production systems is usually a bad idea).

As an engineering manager, have you ever seen an engineer:

  • write unit test coverage for logging but not tests if the feature actually works?
  • merge code but always forget to deploy?
  • have lots of opinions, arguments, and criticisms in meetings but never write code?

A manager observes, actively listens: Is there a pattern? An unvoiced concern or problem?

Then a manager shares with the right people a distilled summary of what's going on, and what change is needed.

Trust and credibility is built by turning pieces of information into action and results.

Mindset of a "legacy manager"

  • How many people are in my organization, and how do I get more?
  • Hard work is measured by who sits the longest at their desk
  • Counting the output of widgets (instead of the outcomes)
  • Uses biases (especially pre-conceived) and argumentativeness (or "winning")

  • jumping to a conclusion about who is the decisionmaker; the blame game

  • One on ones and alignment are overhead - they get paid, don't they?

    • Compliments and praise are over-rated, it's their job!
    • Why should I develop someone's career when they'll just use it to leave? (or "that's HR's job")
  • I should send them my random thoughts at any time, day or night - it's their job to be available and figure it out
  • Unnecessarily going fast and taking risks - activity theater
  • (over) committing when there's any doubt of followthrough
  • Stay in my lane, keep my head down, and mouth shut: enforce that for others too
  • premature public announcements!
    • spreading gossip, misinformation, or disinformation

If reading these things makes you uncomfortable, consider reflecting on the ever evolving nature of the knowledge worker

A Modern Manager of Knowledge Workers

A modern manager understands the symbiotic nature of talent and an organization, genuinely finds alignment and valuable opportunities (including when someone's career leads them to another role - even outside of the company), and communicates clearly.

Solving the problems of your "1st Team"

Managing people and resources is leverage to solve business problems. Your peers - your first team - are telling you what they (and the business) need. If you only do what your manager tells you, just an extension of only your manager's asks...

then you're not proactive, not aligned to the business priorities, and not a team player with others genuinely trying to solve company problems.

https://www.youtube.com/watch?v=BjE_mPoZPSg "Team #1" by Patrick Lencioni

A helpful checklist:

  • do your direct reports know what your quarterly or monthly goal is? How they can contribute to success?
  • do you communicate clearly what you expect?
  • when did you last give each direct report a compliment in private? in public?
  • when have you invested in your direct reports: coached them through something? they learned something new? received a raise or a promotion?
  • expansive view of everything they do to make their organization and group successful

Litmus test questions about trust:

  • do your direct reports feel safe enough and are you curious enough, to learn the names of their loved ones, including pets?
  • do your direct reports feel safe enough to bring you problems and give you feedback?

Recognize people for who they want to be, build trust every day

Prioritizing career development over business needs

If you are prioritizing your own career development or more charitably your direct report's career progressions at the expense of the business outcomes, then you are clearly in a "local maxima".

Aligning what your direct reports or you need to develop along with business priorities is good management.

Don't mistake balance for equality...

Thought experiment: if every manager focused primarily on their direct reports' career development - giving them opportunities to fail and learn and explore - while neglecting what the business needs... and the business fails.

Then nobody has a career to develop!

Challenging Moments and Hard Decisions

If the business is failing then saving the business - which is everybody's job, may be more important than whether your direct report gets a promotion or retained.

Avoiding needless attrition is common sense, but in a crisis, priorities compress and trade-offs get explicit.

Is a Director just Manager++ or VPE--?

Director as Manager++: you're a "super manager" who happens to have managers reporting to you. This works when the business is stable and the primary value is execution consistency. It fails spectacularly when the organization needs strategic pivots or cross-functional coordination.

Director as VPE--: treated as a junior executive, expected to think about business problems, tradeoffs, and org design. This works when the company is scaling or transforming. It fails when you neglect the humans in your organization because you're too busy in leadership meetings.

As a director, the extra layer of indirection between "leadership" and "front line managers" changes everything.

Director reality: all the problems are now your problems. Bubbling up from the front lines, and trickling (or crashing ;) down from above.

Understand the value stream from initial ideas and stakeholders through design and requirements build development, testing deployment, and monitoring.

Have metrics (or a dashboard) doesn't have to be thorough, just enough to give you a warning signal to investigate.

Managing a Manager

Everybody has a first time they became a manager (and the role is already hard!), a great leader helps people nagivate the change.

Hopefully you've learned to become a great people manager before becoming a "manager of managers" - it's never too late!

And just like a Manager is not effective trying to do every one of their direct report's jobs, someone Managing a Manager has to focus on teaching about people management (not taking over or micro-managing).

As a concrete example, when hearing one of my managers bring up not feeling connected to a new direct report, we discussed that there actually many ways to have a one-on-one:

  • the direct report has their own agenda
  • John offers a "choose your own adventure" of topics (e.g. how can I help unblock something? larger context in the org or business? career conversation?)
  • the direct report drives with just a stream of consciousness - your job is to actively listen and spot trends and anomalies
  • the manager drives (when very comfortable with their manager, likes someone else exposing them to new topics/ideas)

Seek first to understand

  • Be curious about their perspective: value and opportunities they see, challenges they experience, approaches they've tried
  • help them construct their own individualized plan for success

For a first time front-line manager the sub-graph of the organization is small: often focused "downward" to just their direct reports.

Teach and encourage (even to the point of discomfort) people managers to navigate peer relationships and "managing up":

  • invest time and build relationships before you need them
  • understand other disciplines and roles, what do they need to succeed?
  • ensure you listen first, ask and follow through on supporting them

An existential lesson is that Managers create a predictable sub-system.

Even Managers with innate people relationship talent have to learn to become systematic, have frameworks, and regular feedback (even difficult conversations) to keep things on track.

What Directors Must Learn (That Managers Can Ignore)

A manager asks "What should my team work on?"

A director asks "What can only I do, what should I delegate, and what can wait?"

Be explicit in what level of delegation you are actually expecting: https://www.jillwetzler.com/resources/delegation

Know what the org/business needs from your domain. A manager can get away with "my team ships good code." A director cannot stop there. You need to understand revenue, runway, competitive positioning, and which parts of your technical portfolio directly impact those things.

Proactively share your group's status and health. Your manager (VP, CTO, whoever) has limited attention. They need a signal, not a firehose of details. Learn to communicate "we're on track" or "we're at risk because X" in 30 seconds or less.

Improve your group's productivity. Not activity, Outcomes! This requires understanding what outcomes matter (see above) and then relentlessly removing obstacles to those outcomes.

Efficiency and cost. At the manager level, headcount is something that happens to you. At the director level, you're accountable for spend. Every engineer-month is real money invested, are you getting a return?

Engineering Leadership is Systems Thinking About People

Here's a mental model to consider:

A great senior engineer knows which service to modify, which file to open, which lines of code to change to have the most impact on the system.

A director of engineering knows which people to talk to, what to say to them, and how to sequence those conversations to have the most impact on the organization.

What is the goal of the system, the weaknesses and greatest opportunities?

  • growth and transformation
  • succession planning
  • personality alchemy, blending skills and experiences
  • technological investment: balancing innovation and legacy

Directors think in "teams", not "individuals"...

A manager thinks about "Retention and Results", a Director has to systemize and scale:

  • reproducible successes
  • manage risk
  • determinism with people

Find the right people who understand the high leverage techniques (technology or organizational), find/create the right org structure to put those people in the places where they can do impactful work with the sense of ownership and accountability.

Get the right people on the bus, in the right seats

https://www.jimcollins.com/concepts/first-who-then-what.html

Culture: The Thing Directors Actually Own

As a manager you participate in culture, yet at the director level, you shape it.

Outputs vs Outcomes: are you a metrics and process driven organization, or results and outcome driven?

Engineering best practices: are they documented? Enforced? Evolving?

Learning tools: books, video courses, internal wikis. Do people have access and do they know they exist?

Lunch and learns, hackathons, team and company demos: these don't happen by accident, make space for them and protect that space when delivery pressure mounts.

Fun events: connecting people matters. Remote-first makes this harder and no longer optional.

Interviewer training: being an interviewer is a completely different skill. Do your people know how to do it? Are they calibrated?

Ownership: testing, "you build it you run it," production responsibility. Is this just a slogan or a regular practice?

Blameless retros and continuous learning: do people feel safe raising concerns? Do incidents lead to learning or blame?

Psychological safety: "see it, say it." If people can't raise problems, the problems don't go away - they just become surprises.

  • Embracing difficult conversations and feedback, navigating how to have them even when it's uncomfortable but you need to have a conversation

https://rework.withgoogle.com/intl/en/guides/understanding-team-effectiveness

The spotlight and microphone: what is your organization celebrating? What is getting rewarded as "high performance" and ensuring the optics match reality - help teams see and participate in the wins

Is something missing?

Of course =)

There's no complete guide because it has to be guided by what your organization needs - even as your organization changes.

When considering becoming a people manager or a Director, the promotion is not simply "more work", these are truly different challenges and roles that deserve careful and open minded learning.

Appendix of Checklists

Manager Activities

Ensuring the following for their team members:

  • roadmaps, sprints
  • tracking work and bugs and launch checklists
  • on-call, runbooks, postmortems
  • accountability on projects and deliverables
  • team and project retrospectives
  • how to identify when team has toil, waste? (not all "work" is equal)
  • individual and team recognition
  • ownership, alignment and growth
  • regularly scheduled 1:1s (including taking notes and documenting action items; sharing those for transparency)
  • approving expenses and PTO

The Unseen Work of a Director

Things a manager rarely thinks about that become a director's problem:

  • Ensuring compliance and IC training
  • Access permissions and SSO/audit improvements
  • Helping with SOC2 or other compliance and external audits
  • Vendor contracts and licensing (including open source libraries)
  • Tools and reports to analyze/audit vendors and usage
  • Frameworks to gather data across many systems - not just deployments and incidents, but interactions with other teams and departments
  • Cleanup and deletion of old or extraneous systems
  • Approving PTOs and building a culture of communication (and coverage) during vacations
  • Training your managers - and other people's managers too (yes, you're responsible for this now)
  • Coordinating with other departments on how they achieve their goals and their needs
  • Compensation analysis with HR
  • Standardization and analysis/improvement of hiring with Recruiting
  • Creating and Maintaining the career ladder

None of this is glamorous. All of it matters.

The Middle Manager Playbook

Here's what actually happens when you're the quintessential middle manager:

  1. Receive a Vision or Strategy from above (leadership, maybe a passthrough from the board)
  2. Ask questions to gain understanding: context, scope, expectations, timelines, risk, feasibility
  3. Write it up in your own words (refer back to the authoritative source doc)
  4. Understand dependencies and coordination - go from ideas to a plan
  5. Get feedback from your "right hand person" and trusted peers - this is where being cross-functional is a necessity
  6. If necessary, convey that feedback all the way back up to the top
  7. Write up comms (explain the Why!)
  8. Ensure there are milestones, clarity on who does what (in what order), who the leads/champions are, where/how to ask questions and raise issues
  9. Roll it out to your org, capture questions and feedback
  10. Have scheduled check-ins, keep the project on track, and check in "upward" to understand changes in priority, urgency, or scope

It looks obvious written down but it is not obvious when you're in the middle of three conflicting priorities with incomplete information from above and limited capacity below.

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leadership

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