“I have two months to deliver.” An execution plan

Kent Dahlgren
6 min readMay 27, 2022


I hear this frequently:

“We have two months to deliver.”

“I have two months”

You say you have two months, which tells you that you have 60 days.

Actually, you only have seven or eight weeks, which you might think is the same thing, but it’s not.

“I have seven to eight weeks”

It’s likely that you’re reliant upon volunteer assistance, so you’re not going to get “full time” effort.

Between full-time employment, side hobbies, and volunteer efforts: everybody is “working part time,” but many people believe that they are able to deliver full-time quantity and quality.

They are wrong, because people are not efficient with their time.

Most people pad their schedules with long-winded discussions, which allows them to overlook the fact that they consistently over-commit and under-deliver, and when they participate in a subculture that embraces these same qualities, it becomes acceptable to consistently fail to meet expectations, because “it’s what everyone else is doing.”

But this is a start-up, activist endeavor, and your credibility is on the line.

So either you need to deliver as promised (in two months), or you need to employ a “fail-fast“ tactic so you can inform other parties early, ideally giving them no fewer than six weeks notice so they are not left feeling flat-footed.

Let’s talk about the size of your core team.

Two is fine, three is good, and five is ideal, provided they are all consistently able to deliver; anything beyond that is diminishing returns.

“It takes a village”…but not necessarily a large one

Let’s talk about team throughput, or the ability for the team to actually deliver.

“Two to three small-to-medium-sized tasks per week”

At most, a team of about three to five part-time contributors are only able to deliver upon two or three small to medium tasks, per five day week.

Note that a small to medium task is not “a marketing plan,” “a business plan,” or “build a website.”

Keep task size small to medium, and therefore realistic

People consistently under-estimate the amount of work necessary in a task, and they over-commit relative to the actual ability to deliver for a variety of reasons I’ll elaborate upon in a moment.

And so if you are disciplined in the definition of each task, you will find that over the course of the next seven weeks you are lucky if you will deliver adequately upon 18 to 21 tasks.

Keep expectations right-sized by being realistic: you won’t deliver upon all tasks

These tasks need to be organized so they reveal sequencing, dependency, and budgetary needs, which will imply a certain order, and if you are going to implement a “fail-fast” tactic, then you will need to make sure that you select the most critical tasks for execution within the first two to three weeks.

It’s likely that one task cannot be started until another one is completed: “sequencing and dependency”

Let’s talk about team efficiency.

In my experience, a smaller team is better than a large one, especially if the team is given to superfluous discussion (hint: they ALL ARE).

I tend to staff multiple teams numbering no greater than two to three, with modest overlap, assigning a single task to each team for release sequence.

This is precisely how I design “hunter teams” for hacking exercises against certain targets; they are autonomous, high-performing, but are also very resilient to disruption.

An example of how I structure small execution teams in other, more kinetic contexts. The model works

If a small team fails to execute because they spent the past week talking about their take on current events, ideally you can fire up a backup team and have them execute concurrently, assuming you’ve rallied enough volunteers.

This, by the way, is why I am so insistent that people focus on executing upon that which was discussed in this brief video:

Let’s be clear: many people don’t invest in building a cohort of people who share a certain fire for delivering upon a vision. Unfortunately, most people would prefer to couple themselves to others so they can claim credit for a success to which they minimally contributed, and those people drag a project down.

You need to identify and remove those people as soon as possible.

A joke:

A pig and a chicken are having a talk, and the chicken says “we should have ham and eggs for breakfast tomorrow. I’ll bring eggs; what are you bringing?”

The point is: the chicken is providing a contribution, whereas the pig is making a sacrifice. You want to identify and remove as many chickens as possible from your core team.

But you’re the boss, so I would get stickies, and write each task on a separate sticky, assembling them on the desk in front of you so you can begin to get a sense of sequencing, timing, and “fail-fast.”

You can put your initial on every single sticky, because you might be all you can count on, and then begin thinking of the two or three others that you can count on almost as much as you can count on yourself.

In my almost 40 years experience, the people you can count on most are almost always older women. More often than not: men are a waste of time. They talk too much and do almost nothing. Nine times out of ten, the chickens are men.

Execution tempo.

Let your volunteers know that this will be your execution plan, in the event that they are interested in helping you preserve your reputation:

Monday through Friday there are daily check-ins, with meetings that last no longer than 10–15 minutes.

Q: how do you eat a whale? A: a bite at a time.

There’s no superfluous discussion, merely an acknowledgment that progress is being made on each task, and the immediate identification of any barriers that are encountered.

Once a week have a meeting that lasts just a little bit longer, maybe 30–45 minutes, for a more high context discussion around what tasks will be selected in the following week, as well as a ruthlessly-honest review of progress and barriers experienced in the prior week.

If you have the discipline to execute within these parameters, by about two to three weeks you will know with about 60 to 70% confidence if you are going to be able to deliver upon your plan.

If you are not confident you can deliver, you are doing yourself a favor by informing others of your inability to pull off your plan, which other people appreciate a lot more than you might realize.

Again, most people over commit and under deliver, they consume most of their productive capacity engaged in superfluous activities because they and other participants believe them to be productive.

To that end, let’s talk multitasking.

Most people believe they are more productive because they are multitasking. This is false; multitasking is a lie.

It’s true: you cannot multitask without impairing your own performance

When people are multitasking, they are listening to respond rather than listening to understand.

They are scanning the conversation for keywords, which makes them prone to misunderstanding critical information, and they believe they fully engaged in a conversation when they did not, leading to misunderstandings that grow worse over time.

Those who participate in multitasking are frequently most prone to overcommit and under deliver because they seek the catharsis of busy work, which robs them of the ability to deliver concrete action in the intermediate to long term.

Good news: as a manager, you’re able to quickly identify those most likely to impair team execution simply by watching them during each meeting.



Kent Dahlgren

Product management fix-it guy. World-famous people skills. Extremely small hands. (edit) marketing lady says I’m also supposed to say “CEO of software company”