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Why don’t we have a strategy?

cutlefish.substack.com

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Re: Why don’t we have a strategy?

#61
post #49

Earlier quoted context omitted.

i agree, but think timelines are a practical necessity of business. this is why we get so much half-baked/unfinished stuff being released. and this is where the trade-offs happen that dilute or misdirect an otherwise sound roadmap/strategy. some exec needs shit done so he can present to his boss and get his nice bonus, then jump ship before they realise its a clusterf*ck.

I don't disagree that timelines are important. However, here is the problem I consistently see: Wrong Way: Most roadmaps contain timelines that are "We're going to build this specific thing and we're estimating it's going to take this long" (Even worse is if they're specifically bucketed by quarters with strict cut offs). Isolated estimates of how long something will take will always be wrong because it doesn't accou…

[deleted]

Re: Why don’t we have a strategy?

#62
post #14

The overwhelming majority of “strategies” are just rigid sequences of time bound outputs/shit you want to build, that always end up being wrong and needing to change because of new information coming in. Strategy needs to be: - We’ve identified this deep problem in the world that needs to be fixed - We want to bring the Vision to life where that problem is gone (a big bold future state of the world). - We believe bri…

Disagree. Short term - todo list, Mid term - features list, Long term - future milestones. All three together form your roadmap. All three guided by macro goals.

Re: Why don’t we have a strategy?

#63
"A Strategy" is the problem. Strategy is an activity, a process, a rigorous engagement with reality, a forging of choices. It's not a "vision" or a "charter" or a document. It's an action. It's playing with other forces in the world that can be adversaries, obstacles, and allies. It's the thing you go back to when your assumptions are challenged and efforts don't work. Purpose informs strategy. Facts and intelligence inform strategy. Beware "strategy theater" and "Potempkin artifacts" like vision statements, roadmaps, and policies that comfort despite an absence of strategy work.

Re: Why don’t we have a strategy?

#64
post #49

Earlier quoted context omitted.

I don't disagree that timelines are important. However, here is the problem I consistently see: Wrong Way: Most roadmaps contain timelines that are "We're going to build this specific thing and we're estimating it's going to take this long" (Even worse is if they're specifically bucketed by quarters with strict cut offs). Isolated estimates of how long something will take will always be wrong because it doesn't accou…

Great comment. "futures not features" is a gem!

"Outcomes not outputs" is another similar way of stating it

Re: Why don’t we have a strategy?

#65
post #49

Earlier quoted context omitted.

i agree, but think timelines are a practical necessity of business. this is why we get so much half-baked/unfinished stuff being released. and this is where the trade-offs happen that dilute or misdirect an otherwise sound roadmap/strategy. some exec needs shit done so he can present to his boss and get his nice bonus, then jump ship before they realise its a clusterf*ck.

I don't disagree that timelines are important. However, here is the problem I consistently see: Wrong Way: Most roadmaps contain timelines that are "We're going to build this specific thing and we're estimating it's going to take this long" (Even worse is if they're specifically bucketed by quarters with strict cut offs). Isolated estimates of how long something will take will always be wrong because it doesn't accou…

Your "right way" is the right approach to anchor on but in reality it never works out as nice as it sounds. Common problems:

1. You have some projects that are rigorously time bound (e.g. we absolutely need to ship X by Y date). Maybe scope is negotiable a bit but you definitely need results by a certain date.

2. Implicitly all of your work is time bound. Even if you say "we want to get to a 60% reduction in support calls", the follow up question is "by when?". Tons of internal forces (employee reviews, shifting company priorities) shift the framing from "we think a 60% reduction in support calls is a healthy sustainable level for our business, and that is our goal" to "we are targeting a 20% reduction in support calls over the next six months". Then your multi-quarter big-bet projects need to be broken down into phases which won't have an impact on the support calls by themselves, so you have to take ship goals or create other goals to capture that work (not great)

Re: Why don’t we have a strategy?

#66
post #65
post #49

Earlier quoted context omitted.

I don't disagree that timelines are important. However, here is the problem I consistently see: Wrong Way: Most roadmaps contain timelines that are "We're going to build this specific thing and we're estimating it's going to take this long" (Even worse is if they're specifically bucketed by quarters with strict cut offs). Isolated estimates of how long something will take will always be wrong because it doesn't accou…

Your "right way" is the right approach to anchor on but in reality it never works out as nice as it sounds. Common problems: 1. You have some projects that are rigorously time bound (e.g. we absolutely need to ship X by Y date). Maybe scope is negotiable a bit but you definitely need results by a certain date. 2. Implicitly all of your work is time bound. Even if you say "we want to get to a 60% reduction in support…

Great comments:

> 1. You have some projects that are rigorously time bound (e.g. we absolutely need to ship X by Y date). Maybe scope is negotiable a bit but you definitely need results by a certain date.

In this case, you explicitly call out that roadmap item, and label it as "this thing will win out and other initiatives will be delayed if this thing goes sideways"

> 2. Implicitly all of your work is time bound. Even if you say "we want to get to a 60% reduction in support calls", the follow up question is "by when?". Tons of internal forces (employee reviews, shifting company priorities) shift the framing from "we think a 60% reduction in support calls is a healthy sustainable level for our business, and that is our goal" to "we are targeting a 20% reduction in support calls over the next six months". Then your multi-quarter big-bet projects need to be broken down into phases which won't have an impact on the support calls by themselves, so you have to take ship goals or create other goals to capture that work (not great).

Yes, you're right, I didn't write that one clearly. For outcomes like that, you should have defined "come up for air" dates where you measure and determine whether you keep going or call it as good enough/not worth it to continue and then move on to other things.

Re: Why don’t we have a strategy?

#67

Interestingly enough -- well, to me, at least -- I came across this introductory video[1] last night from HBR about the differences between strategy and planning. It's piqued my interest enough to look more into it. [1] https://www.youtube.com/watch?v=iuYlGRnC7J8&t=325s

Thanks, that was educational to watch.

Re: Why don’t we have a strategy?

#68
I’m not convinced.

Here’s my theory for explaining the lack of strategy in many organizations: Many people are incapable of thinking into the future and imagining the possible outcomes of various courses of action. The let’s-just-take-it-2-weeks-at-a-time-and-see-how-it-goes process known as “agile” has let these people assume positions of power. If you try and switch back to a more long-term strategic working model they will fight tooth and nail for their positions, which they understand they are not competent to hold if seeing more than 2 weeks into the future is part of the job description.

Re: Why don’t we have a strategy?

#69
post #35
post #34

> The problem is that there are disincentives to thinking strategically. To me the problem was that nobody around could even explain what does it mean. It's such a vague word nowadays, and even when you really want to craft a strategy for your organization, you end up watching videos telling you to outline your values, write a mission statement and set SMART goals. Thanks to some coments on HN I've read "Good strateg…

The question is around scope, if you are building a strategy for yourself or your team - set smart goals. If you are building a strategy for an organization, then set KPIs. If you are building a strategy for a 100+ person organization, then you talk about vision.

That's what I'm talking about – explanations like yours are abundant (no offence).

Following your advice, let's say I set SMART goal for myself - "Increase number of books I read per month to 10 by the end of the year". It's specific, measurable, achievable, relevant and time-bound". It's still a goal, not a strategy.

Re: Why don’t we have a strategy?

#70
post #56

I always have interesting discussions during job interviews when I answer the old "where do you see yourself in five years" or when discussing my non-linear/standard career path. I'm a bit of a fan of Mintzberg's view on strategy when it comes to career "planning" and technology companies (I'd recommend his book "Rise and Fall of Strategic Planning"). He uses a garden metaphor and basically says let everything grow a…

> Different situations require different approaches.

I very much agree. When it comes to developing a meaningful strategy, this depends largely on the details of what is at issue.

Imagine some really demanding business idea that could perhaps be put into reality towards the end of this century, like astroid mining or a hotel on the moon. Does it already make sense to found a company, collect money and work on a strategy? If there are too many moving targets or the goal is just too large or too distant or demands too many ressources, there may not exist a feasible strategy, no matter how hard we think about one.

At the other end of the spectrum think of some boring, but established business idea, like opening a restaurant or starting an organic farm. In this case, there exist thousands of role models to learn from. Success is not guaranteed, but one does not need to re-invent the wheel to outline a strategy and get started.

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