What type of decisions do you find most difficult to make?

[andrey.kessel]

Hi everyone. What type of decisions do you find most difficult to make? Deliberately open-ended question to not constraint a conversation. (for context - we are building automated tools for SME owners, so looking to hear the groups like this one to inform priorities/sequence),

 

[fisicx]

Hi everyone. What tupe of decisions do you find most difficult to make? Deliberately open-ended question to not constraint a conversation.

(for context - we are building automated tools for SME owners, so looking to hear the groups like this one to inform priorities/sequence),

How many biscuits to have with my mid morning tea.

 

[andrey.kessel]

How many biscuits to have with my mid morning tea.

Recorded into the database, thanks

 

[Lucan Unlordly]

In an interview for a job I was presented with a set of questions and given 10 minutes to write down the answers. I finished 19 of them quickly then returned to the first.
Q: Given the opportunity, would you A; Stop the next world war or B: Solve all the worlds health problems?

On the basis that I took several minutes thinking about an answer it was determined that I didn't like making decisions! I was tempted to ask if, given the choice, the interviewer would prefer to balance a Cowpat on his head for evermore or stand barefoot up to his ankles in xxxx!

I don't like stupid questions.

(PS: It's a glass, it has water in it - end of story)

 

[JEREMY HAWKE]

What lunch that wont make me a fat boy

 

[fisicx]

@andrey.kessel - the problem with a question like yours is you are at the back of a long queue of posters who have been asking similar question both here on UKBF and many other platforms for years.

What I find difficult others may find easy. Some don't even consider difficulty, others can't make a decision about when to read their emails. Decision making cannot be automated. All you can do at best is advise on options using the current information (which may change as the day progresses).

 

[WaveJumper]

Lets switch it around what do you think are the difficult decisions and the thoughts behind how your automated tools may help

 

[MikeJ]

You should build a tool to help answer the question "What type of decisions to business owners find most difficult to make?"

You appear to be building something and don't know the purpose of it yet, which I think is a brave* thing to do.


* A "Yes Prime Minister" type of brave.

 

[andrey.kessel]

@andrey.kessel - the problem with a question like yours is you are at the back of a long queue of posters who have been asking similar question both here on UKBF and many other platforms for years.

What I find difficult others may find easy. Some don't even consider difficulty, others can't make a decision about when to read their emails. Decision making cannot be automated. All you can do at best is advise on options using the current information (which may change as the day progresses).

Thanks for your answer. I am not trying to automate decisions, totally agree with you that most of it can't be automated. And also fully agree with a lot of people asking. What I find is that there is a lot of generic fluff in this (and many other areas may I add) that is totally unhelpful and misdirected. I am actually a small business guy and rather pragmatic, so trying to do tools that have a chance of being useful. In the context of decisions the idea is to help check what, if anything, has been missed from consideration and also thinking about helping people build a support system (not me, for clarity). That can be automated and is more diagnostic/checklist type of thing.

 

[andrey.kessel]

You should build a tool to help answer the question "What type of decisions to business owners find most difficult to make?"

You appear to be building something and don't know the purpose of it yet, which I think is a brave* thing to do.


* A "Yes Prime Minister" type of brave.

Thank you for the input
I'd be interested to know how you came to this conclusion - based on what information? To comment in the same tone - you appear to be making judgements about something you don't really have any information about.
Also * a faily "Yes Prime Minister" type of thing, no?

 

[fisicx]

Thanks for your answer. I am not trying to automate decisions, totally agree with you that most of it can't be automated. And also fully agree with a lot of people asking. What I find is that there is a lot of generic fluff in this (and many other areas may I add) that is totally unhelpful and misdirected. I am actually a small business guy and rather pragmatic, so trying to do tools that have a chance of being useful. In the context of decisions the idea is to help check what, if anything, has been missed from consideration and also thinking about helping people build a support system (not me, for clarity). That can be automated and is more diagnostic/checklist type of thing.

This is still very confusing. Can you post a working example of your tool. Use a typical business activity like assessing a potential client.

 

[andrey.kessel]

Lets switch it around what do you think are the difficult decisions and the thoughts behind how your automated tools may help

Thank you for responding.

As I mentioned in another answer, in the decision area the idea is to have a diagnostic that helps check if something important was misseв while considering a decision. Obviously, not for simple decisions, but more for impactful ones. Hence, the original question - and it obviously was too open ended (my mistake) since I was trying not to lead on the answers.

A couple of examples of questions that come back to me (in dofferent forms)
Should I Focus on Growth or Profitability?
Should I Hire, Automate, or Stay Lean?
Should I Build a Management Team or Keep Running It Myself?
Should My Business Specialise or Serve a Broader Market?

 

[andrey.kessel]

In an interview for a job I was presented with a set of questions and given 10 minutes to write down the answers. I finished 19 of them quickly then returned to the first.
Q: Given the opportunity, would you A; Stop the next world war or B: Solve all the worlds health problems?

On the basis that I took several minutes thinking about an answer it was determined that I didn't like making decisions! I was tempted to ask if, given the choice, the interviewer would prefer to balance a Cowpat on his head for evermore or stand barefoot up to his ankles in xxxx!

I don't like stupid questions.

(PS: It's a glass, it has water in it - end of story)

Lucan, thank you for your input. 100% with you about stupid questions. feel the same about stupid answers.

 

[fisicx]

Thank you for responding.

As I mentioned in another answer, in the decision area the idea is to have a diagnostic that helps check if something important was misseв while considering a decision. Obviously, not for simple decisions, but more for impactful ones. Hence, the original question - and it obviously was too open ended (my mistake) since I was trying not to lead on the answers.

A couple of examples of questions that come back to me (in dofferent forms)
Should I Focus on Growth or Profitability?
Should I Hire, Automate, or Stay Lean?
Should I Build a Management Team or Keep Running It Myself?
Should My Business Specialise or Serve a Broader Market?

For any tool to help with any of these it would have to ask a whole load of questions the answers to which may generate even more questions. Every business is going to be different with many nuances that can affect the outcome.

Do you have a demo members here can look at?

 

[andrey.kessel]

This is still very confusing. Can you post a working example of your tool. Use a typical business activity like assessing a potential client.

@fisikx,
You're right, it's confusing. I'm still in the process. But for example, assessing a potential client was the kind of thing that my question was after - I do not have anything for that, at least not yet. I'm also working on making this much more specific to common business situations/questions. So far, I have a bunch of more generic ones (since it's coming from a systemic perspective of building the diagnostic).

I gave a few examples of decisions/questions in another answer (they are from the "stuck between options" situations as I call them)

It says I can't post links, is there a way to do that to give you what you asked?

I appreciate your trying to take things seriously and your time/mental cycles.

 

[andrey.kessel]

For any tool to help with any of these it would have to ask a whole load of questions the answers to which may generate even more questions. Every business is going to be different with many nuances that can affect the outcome.

Do you have a demo members here can look at?

Every business is going to be different with many nuances that can affect the outcome. - totally. I am not as naive as to try to do the assessment of the business

For any tool to help with any of these it would have to ask a whole load of questions the answers to which may generate even more questions. - this depends on perspective and questions

I do not aim to assess the business. I work with a decision itself looking at it from system design view.

 

[andrey.kessel]

And to address the question that has not been asked but may have been thought, the diagnostic is currently free and I think will remain free. So, I'm really mostly looking for an answer to the question I asked and the feedback.

 

[StrategyDoctor]

I think part of the challenge with the question is that there isn’t a universal answer.

As others have already pointed out, every business is different and what feels like a difficult decision for one owner may be straightforward for another.

That said, in my experience SME owners generally do not struggle with making decisions. The bigger issue is often that they “don’t know what they don’t know”.

Most founders are experts in their product or service, but not necessarily in finance, HR, tax, operations, logistics, compliance, or organisational design. Problems usually appear when a blind spot turns into a consequence - unexpected tax bills, cash flow pressure, poor hires, operational strain from growth, margin erosion, etc.

A large part of my role working alongside SME owners is effectively being the wingman:
“Have you considered…?”
“Did you know this changes if…?”
“What happens if the assumption is wrong?”

This week alone I picked up an issue in a client’s accounts before filing which likely saved them around £5k in unnecessary tax exposure. They couldn’t make the “right” decision because they didn’t know the issue existed in the first place.

Most good business owners are perfectly capable of making decisions. The difficulty is that they are often making them with incomplete information, exhaustion, bias, time pressure, or without external challenge.

 

[Lucan Unlordly]

Lucan, thank you for your input. 100% with you about stupid questions. feel the same about stupid answers.

Yes, but preferable to no answers?

 

[ES16]

Yes, but preferable to no answers?

Hi everyone. What type of decisions do you find most difficult to make? Deliberately open-ended question to not constraint a conversation. (for context - we are building automated tools for SME owners, so looking to hear the groups like this one to inform priorities/sequence),

One of the hardest decisions for SME owners is deciding where to spend limited time, money, and attention. Most decisions are not clearly “right or wrong” they’re trade-offs between growth, stability, cash flow, and risk.

A few examples I see repeatedly:

• Hiring vs. staying lean
• Investing in marketing without guaranteed ROI
• Choosing between short-term revenue and long-term brand building
• Delegating critical work they used to control themselves
• Deciding which opportunities to say “no” to
• Pricing decisions, especially when competitors race to the bottom
• Technology adoption - knowing what actually saves time versus what becomes another tool to manage

Another difficult category is decisions with incomplete data. SME owners often have to move fast without enterprise-level analytics, so many decisions become intuition-driven under pressure.

If you’re building automation tools, I think the biggest value comes from reducing decision fatigue, not just automating tasks. Owners usually don’t need “more dashboards” - they need clarity, prioritization, and confidence in the next action.

 

[Chris Ashdown]

The ones I hesitated on far to long, as I was scared of change

 

[Mark T Jones]

In today's climate, the biggest decision revolves around how to filter AI bollox from solid, personal advice.

Usually pretty obvious (because the AI merchants don't actually bother to edit or adapt), but I suspect there will be stead creep...

 

[davidleo7557]

In today's climate, the biggest decision revolves around how to filter AI bollox from solid, personal advice.

Usually pretty obvious (because the AI merchants don't actually bother to edit or adapt), but I suspect there will be stead creep...

I get what you mean, it’s getting harder to tell what’s genuinely thought-through and what’s just generic AI output.

I think the key is still the same as ever though—look for lived experience, nuance, and whether someone is actually engaging with the specifics of the situation rather than giving a one-size-fits-all answer.

 

[EnterprisePro]

I have a really silly one. I've been burying my head in the sand about getting us out of the Microsoft ecosystem. We use a lot of it though, from device management (MDM), compliance, SharePoint, Outlook, Teams, Entra... and so on. Its not straightforward for us to get out of MS and im guilty of pushing the decision to Q4 each year and then the following year, but at some point we just might go fully Linux.

 

[andrey.kessel]

I think part of the challenge with the question is that there isn’t a universal answer.

As others have already pointed out, every business is different and what feels like a difficult decision for one owner may be straightforward for another.

That said, in my experience SME owners generally do not struggle with making decisions. The bigger issue is often that they “don’t know what they don’t know”.

Most founders are experts in their product or service, but not necessarily in finance, HR, tax, operations, logistics, compliance, or organisational design. Problems usually appear when a blind spot turns into a consequence - unexpected tax bills, cash flow pressure, poor hires, operational strain from growth, margin erosion, etc.

A large part of my role working alongside SME owners is effectively being the wingman:
“Have you considered…?”
“Did you know this changes if…?”
“What happens if the assumption is wrong?”

This week alone I picked up an issue in a client’s accounts before filing which likely saved them around £5k in unnecessary tax exposure. They couldn’t make the “right” decision because they didn’t know the issue existed in the first place.

Most good business owners are perfectly capable of making decisions. The difficulty is that they are often making them with incomplete information, exhaustion, bias, time pressure, or without external challenge.

Thank you, thuoghtful , useful and echos my experience too. In fact I didn't phrased it like this for myself, but this is one of the biggest things my diagnostic is doing - checking whether there are gaps.

 

[andrey.kessel]

One of the hardest decisions for SME owners is deciding where to spend limited time, money, and attention. Most decisions are not clearly “right or wrong” they’re trade-offs between growth, stability, cash flow, and risk.

A few examples I see repeatedly:

• Hiring vs. staying lean
• Investing in marketing without guaranteed ROI
• Choosing between short-term revenue and long-term brand building
• Delegating critical work they used to control themselves
• Deciding which opportunities to say “no” to
• Pricing decisions, especially when competitors race to the bottom
• Technology adoption - knowing what actually saves time versus what becomes another tool to manage

Another difficult category is decisions with incomplete data. SME owners often have to move fast without enterprise-level analytics, so many decisions become intuition-driven under pressure.

If you’re building automation tools, I think the biggest value comes from reducing decision fatigue, not just automating tasks. Owners usually don’t need “more dashboards” - they need clarity, prioritization, and confidence in the next action.

Thank you, very good input.. I actually just a few blog posts on growth vs profitability (which is an ultimate tradeoff decision) and doing a few on Hiring vs. staying lean vs automating.
You gave me some very useful directions, apprreciate it!

 

[andrey.kessel]

In today's climate, the biggest decision revolves around how to filter AI bollox from solid, personal advice.

Usually pretty obvious (because the AI merchants don't actually bother to edit or adapt), but I suspect there will be stead creep...

I know, also a time consuming thing, so hard to know what it can and can not do until you try a real task... I have been learning by trial and error myself. Did a few articles in my "AI Clinic", but those are the basics really

 

[andrey.kessel]

To

I have a really silly one. I've been burying my head in the sand about getting us out of the Microsoft ecosystem. We use a lot of it though, from device management (MDM), compliance, SharePoint, Outlook, Teams, Entra... and so on. Its not straightforward for us to get out of MS and im guilty of pushing the decision to Q4 each year and then the following year, but at some point we just might go fully Linux.

ugh onw. Vendor lockin can get brural and expensive and Microsoft has been particularly good surrounding businesses with interlinked parts. Would love for you to try the diagnostic I built to see if it would be useful - it's clearly not about Microsoft, but maybe can help surface a thing or two for this decision. That;s the sort of feedback that would be fold for me