Practical Almanac for Technical Program Managers
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What is an almanac and why should I care?
These notes are an almanac for Technical Program Managers.
An almanac is an annual publication containing vital, tabulated data including calendars, weather forecasts, astronomical information (moon phases, sunrises/sunsets), tide tables, and agricultural planting dates
So, an almanac isn’t something you read straight through and move on from. It’s something you come and reference when you need to predict something long-term, or when the season changes, or when conditions shift, or when something familiar starts to behave differently than expected.
That’s how these notes are meant to work.
Each note captures a recurring pattern in TPM work:
where execution tends to break
how ambiguity shows up
how ownership erodes
where judgment actually matters
how to think about your career journey.
They’re short by design, so they can be consulted in the middle of real work. No need to memorize or commit to memory anything.
This isn’t a framework, a checklist, or a set of best practices. It’s a collection of observations meant to help you recognize situations faster, name them more clearly, and respond with intention.
Like any good almanac, its value compounds over time, not by giving answers, but by sharpening how you see what’s already happening all around you.
As I have said before, we TPM’s are world builders. To build better worlds, we need to see the patterns all around us and react appropriately.
Where do these notes come from?
These notes are distilled from more than 15 years of real-world industry experience working directly as a Technical Program Manager and people leader across multiple companies, teams, and problem spaces.
They are also grounded in years of writing and reflection in this newsletter, capturing patterns that surfaced repeatedly across programs, organizations, and career stages. The ideas here weren’t created in isolation or borrowed from theory alone. They emerged from shipping products, missing timelines, repairing trust, navigating ambiguity, and learning what actually matters in execution, sometimes the really hard and painful way.
Nothing here is hypothetical.
Each note exists because the situation it describes happened more than once.
How to use these notes
These notes aren’t meant to be read once and set aside.
The simplest way to use them is as a weekly practice:
Read one note.
Sit with the reflection.
Apply it to the work you’re already doing.
You can also return to this collection whenever something feels off:
when progress slows without a clear reason
when alignment feels fragile
when ownership gets fuzzy
when you’re tempted to add more process instead of more clarity
You don’t need to agree with every note for it to be useful. If a note makes you pause, reflect, or slightly change how you act in a situation, it’s doing its job. If a note doesn’t do anything for you, that is okay because it is still a data point.
Over time, these notes are meant to sharpen your judgment, not by telling you what to do, but by helping you see what’s happening sooner and more clearly. The biggest impact from these notes I hope is the sharpening of your retrospective and observation skills, something super critical especially when you think about jumping from Mid to Senior to Staff+ beyond TPM roles.
That’s the real leverage in the TPM role - observation, retrospection, action.
So, here we go…
CLARITY: Where most execution problems quietly begin
1. Clarity Precedes Execution
Team failing isn’t always just because they moved slowly. They fail because they move in different directions while believing they’re aligned. Lack of clarity shows up as rework, contradictory decisions, and repeated alignment meetings that never seem to resolve anything. Strong TPMs force clarity early by explicitly naming goals, constraints, and what “done” actually means before execution momentum hides or masks the unaddressed confusion. Speed without clarity just compounds mistakes faster.
Reflection: Find one area where rework is happening often and trace it back to missing clarity at the start.
2. Clarity Beats Activity
High activity often masks low progress. When teams are busy but outcomes aren’t moving, the problem is rarely effort, it’s intent. Adding more tasks or meetings may feel productive but usually increases noise. TPM leverage comes from removing confusion so existing effort compounds instead of scatters. The fastest teams are often the ones doing less, with sharper focus.
Reflection: Identify one activity you could pause this week without changing the outcome.
3. Expectations Shape Outcomes
Misaligned expectations cause more damage than missed dates. When different stakeholders carry different definitions of success, every update becomes disappointing to someone. This shows up as surprise reactions late in delivery, even when progress was visible all along. TPMs prevent this by making expectations explicit early and revisiting them as context shifts. Expectations decay unless actively maintained.
Reflection: Reset/Reconfirm expectations on one deliverable before the next milestone. Do you see the impact.
4. Documentation Is a Thinking Tool
Documents are more than just records of decisions; they are tools for making them. Weak docs restate usually state what’s happened; strong docs force choices and surface assumptions to help see where things need to go before it’s expensive to be make the pivot. If a document doesn’t change how someone thinks or decides, it’s probably missed the mark. TPMs use writing to sharpen clarity, not to memorialize confusion.
Reflection: Re-read one document you used to push for a decision or trade off; did the document hit that goal, why or why not.
5. Early Signals Matter
Large failures are usually preceded by small inconsistencies. Repeated questions, vague answers, subtle scope drift, or quiet discomfort in meetings are early warning signs. Ignoring these trades short-term comfort for long-term risk. Strong TPMs act on weak signals while intervention is still cheap. Waiting for certainty usually means waiting too long.
Reflection: Act on one weak signal you’ve noticed but haven’t named yet.
6. Clarity Is Preventative Work
Preventing confusion rarely looks impressive. It doesn’t produce artifacts, demos, or metrics. But clear framing early avoids downstream churn, escalation, and burnout. This work often happens before anyone asks for help, which makes it easy to undervalue. Experienced TPMs do it anyway because they’ve seen the cost of skipping it.
Reflection: Clarify one ambiguous area proactively instead of waiting for it to break.
7. Communication Is Design
How information flows shapes behavior just as much as incentives do. Poor communication creates friction even when intent is good, decisions get misinterpreted, priorities blur, and teams optimize for the wrong signals. TPMs design communication deliberately: what’s shared, when, with whom, and in what form. Communication left to chance becomes a source of risk.
Reflection: Review how a recent piece of information or decision was communicated and what behavior it produced.
8. Decisions Age
Decisions don’t expire on their own, but their assumptions do. What was correct a quarter ago may silently constrain work today. Old decisions often show up as “mysterious blockers” or unspoken rules no one remembers choosing. TPMs revisit decisions before they become invisible constraints that slow everything down.
Reflection: Revisit one decision older than a quarter and check if its assumptions still hold.
9. Constraints Create Focus
Clear constraints help teams decide faster. Ambiguous constraints invite debate, re-litigation, and scope creep. Many teams argue endlessly because they don’t agree on what’s actually constrained; is it time, cost, quality, or something else. TPMs create focus by naming the real constraint and holding it steady long enough for progress to happen.
Reflection: Name the real constraint your program is operating under right now.
10. Clarity Is the Goal
Everything else, speed, process, tooling, exists to support clarity. Without it, velocity amplifies mistakes and effort gets wasted. TPMs who optimize for clarity first create durable progress even in messy environments. When in doubt, the right move is usually to make things clearer, not faster.
Reflection: Ask yourself what would make the current situation clearer for everyone involved.
OWNERSHIP: Where accountability either sharpens execution or quietly erodes it
11. Ownership Must Be Explicit
When ownership is unclear, assumptions fill the gap. Decisions slow down, work stalls, and accountability only becomes visible when something goes wrong. This often shows up as passive escalation or “I thought someone else had that.” Strong TPMs make ownership explicit early, like who decides, who executes, and who needs to be consulted, even when it feels awkward to spell out. Ambiguity here always costs more later.
Reflection: Rewrite ownership for one area where decisions feel slower than they should. Focus on a single owner who is best suited to that situation. Avoid the RACI trap.
12. Ownership Without Authority Is Fragile
Holding someone accountable without giving them influence creates hidden risk. This imbalance often stays invisible until timelines slip or tensions spike late in delivery. TPMs frequently absorb this gap quietly, which delays fixing the system. Healthy programs align responsibility with decision rights, even if it requires uncomfortable conversations.
Reflection: Map one outcome you own and list which decisions shaping it sit outside your control.
13. Alignment Without Accountability Is Theater
Teams can sound aligned while ownership remains fuzzy. Shared language is often mistaken for shared responsibility. This shows up when everyone agrees in meetings but no one follows through decisively. Alignment only matters when someone is accountable for outcomes, not just participation. Anything else is performance.
Reflection: Pick one “aligned” initiative and explicitly name who owns the outcome.
14. Escalation Is a Signal, Not a Surprise
Most escalations aren’t sudden failures, they’re delayed signals. They usually point to unclear ownership, unresolved tradeoffs, gap in accountability, or missing decision rights. When escalation becomes routine, the system is teaching people to defer responsibility upward. TPMs treat escalations as feedback about design flaws, not personal breakdowns.
Reflection: Look at your last escalation and trace what ambiguity allowed it to reach that point.
15. Shared Ownership Needs Structure
“Shared ownership” often means no one truly owns the outcome. Without structure, collaboration turns into diffusion of responsibility. To develop effective shared ownership clarity on who integrates decisions, who breaks ties, and how disagreements get resolved is needed. TPMs make this shared responsibility real by designing the systems that make the responsibilities of “shared ownership” explicit.
Reflection: Clarify how decisions are made in one area labeled as “shared ownership.” Don’t lean on RACI trap. Keep it simple.
16. Follow-Through Creates Real Ownership
Decisions without follow-through decay quickly. Ownership isn’t just making a call rather it’s ensuring that the call actually lands. This shows up when teams agree in principle but execution drifts quietly afterward. Strong TPMs track follow-through, not to micromanage, but to protect intent.
Reflection: Check one recent decision that hasn’t been reinforced since it was made. Identify the source of this lack of follow-through.
17. Authority Drifts Over Time
Decision rights shift as teams grow, priorities change, and people move roles. What was once clear slowly becomes outdated. This drift shows up as confusion about who can say yes or no and who carry’s the ball when it drops. TPMs periodically refresh ownership assumptions instead of letting them fossilize or when things break down.
Reflection: Update ownership for one area that hasn’t been revisited in months.
18. Ownership Reduces Drama
Most delivery drama thrives in the absence of clear ownership. When no one is clearly accountable, issues turn emotional and political. Clear ownership doesn’t eliminate conflict, but it channels it productively. TPMs use ownership as a preventative tool, not a reaction to failure.
Reflection: Identify one recurring conflict that might disappear with clearer ownership.
19. Accountability Should Be Visible Early
Accountability that only appears at the end of a program is too late. It should be visible throughout execution, in decisions, updates, and tradeoffs. When accountability is clear early, teams self-correct faster. TPMs surface accountability before pressure forces it out.
Reflection: Ask where accountability is currently implicit instead of explicit.
20. TPMs Often Hold the Gaps
TPMs frequently sit in the gaps between formal owners. This is useful short-term but dangerous long-term if left unnamed. Absorbing gaps quietly prevents the system from improving. Strong TPMs make gaps visible so ownership can be redesigned instead of personally carried.
Reflection: Notice one gap you’re holding that should be redesigned to a proper owner instead of endured.
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EXECUTION: Where good intent meets real constraints
21. Execution Breaks at the Edges
Programs rarely fail in the middle of a team’s core work. They fail at handoffs, dependencies, and seams between teams. These edges are where assumptions go unspoken and responsibility gets blurry. TPMs create leverage by reinforcing the edges early, not by micromanaging the center.
Reflection: Identify one seam between teams that hasn’t been explicitly reinforced.
22. Status Is a Lagging Signal
By the time an issue appears in status, the important decisions have already happened. Status captures outcomes, not momentum or decay. Early signals live in hesitation, repeated questions, and subtle scope shifts. Strong TPMs listen for what isn’t being said, not just what’s reported. They tackle these decisions rather than waiting for status for something to be done.
Reflection: Write down one concern you’re carrying that hasn’t made it into status yet.
23. Milestones Hide Risk
Milestones create a sense of control but conceal most real risk. Dependencies drift and assumptions decay between checkpoints. When teams only focus on milestone completion, problems surface too late to recover cheaply. TPMs stay engaged in the in-between moments where risk actually accumulates. They name the implicit and keep an eye on the explicit risks before things go sideways.
Reflection: Look between your next two milestones and name the implicit and explicit risks.
24. Execution Is a Social System
Execution doesn’t happen in a vacuum. Incentives, fear, trust, and ego shape outcomes as much as plans do. Ignoring this leads to repeated surprises that feel “unexplainable” after the fact. TPMs work with human systems, not just schedules.
Reflection: Observe one social dynamic between teams or individuals currently influencing execution more than the plan.
25. Repetition Reveals Structural Gaps
When the same issue keeps resurfacing, it’s rarely a one-off mistake. Repetition signals a structural problem that hasn’t been addressed. Treating symptoms with reminders or escalation wastes energy. TPMs look for the underlying design flaw and fix that instead.
Reflection: Identify one recurring issue and ask what system allowed it to persist.
26. Structure Beats Heroics
Heroics feel good in the moment but don’t scale. When execution depends on individuals saving the day, the system is already failing. Sustainable programs rely on structure that absorbs normal variability. TPMs replace heroics with systems before burnout sets in.
Reflection: Notice where execution currently depends on someone “stepping up” repeatedly.
27. Good TPMs Reduce Surprise
Predictability matters more than speed. Teams can handle bad news if it arrives early, but surprises erode trust quickly. Many execution failures aren’t about missed goals rather they’re about when people found out. TPMs optimize for fewer surprises, not perfect outcomes.
Reflection: Ask yourself where surprise is still likely in the current plan.
28. Timing Matters as Much as Content
The right decision at the wrong time can still fail. Poor timing creates resistance even when the logic is sound. TPMs pay attention to organizational readiness, competing priorities, and emotional context. Execution isn’t just about what to do, it’s about when to do it; when to escalate, when to ask for more resources, when to change the plan.
Reflection: Consider whether the timing is right for a decision you’re about to push.
29. Execution Requires Reinforcement
Agreement is not the end of execution; it’s the beginning. Decisions decay unless reinforced through follow-ups, reminders, and visible action. Drift often happens quietly after alignment meetings. TPMs protect intent by reinforcing decisions until they stick.
Reflection: Reinforce one decision that’s at risk of fading.
30. Execution Is Continuous
Execution doesn’t pause between meetings or milestones. Risk accumulates even when nothing seems to be happening. TPMs stay engaged in the quiet stretches, not just during high-visibility moments. Consistent attention prevents last-minute chaos.
Reflection: Re-engage in one area that currently feels “under control.” Dig deeper, any surprises yet.
JUDGMENT: Where seniority actually shows up
31. TPM Is a Judgment Role
Tools, processes, and frameworks support TPM work, but they don’t define it. The real value comes from judgment; knowing what matters now, what can wait, and what risk is real versus theoretical. Poor judgment often hides behind rigid adherence to process. Strong TPMs are trusted because they consistently make reasonable calls under uncertainty.
Reflection: Think about a recent situation where judgment mattered more than following the process.