Six months ago I put out an offer - to help entrepreneurs process the turmoil and opportunity presented by 2020 and COVID.
Every few weeks I go back through my notes and summarise the recurring themes and conversations.
I hope these questions and ideas spark something useful for you, please let me know how I can help you and your business.
Here’s Part Four, you can also find Part One, Two and Three.

“What advice would you give someone else in your position?”
This is a great question to reset your perspective.
We’re often a hard taskmaster on ourselves, setting unrealistic expectations on what we can reasonably do and in what timeframe.
When we don’t hit these targets, our minds turn to criticism rather than analysis, leading to guilt instead of learning.
On four recent occasions, I’ve asked someone this question when they’ve been self-critical.
Every time, there’s a pause and a nervous giggle.
They realise that if they told someone else to hold these expectations, they’d be a terrible advisor and a bit of a bully.
If you were advising someone else, you’d preach balance.
You’d encourage them to make decisions without apportioning blame.
You’d show them that their fears are overstated.
You’d give them permission to start anywhere, and learn as they go.
You’d tell them not to take things so personally.
Instead of treating yourself as a second-class citizen, what if you listened to your own compassionate advice?

Do we want to pause, pivot or persevere?
Every entrepreneur in the world is navigating the choice of pausing, pivoting or persevering with their businesses.
They might not realise that all three are valid options.
Pausing your business might be a good idea – if there’s no market, no ability to sell your products and services or a lockdown in your area, then why pretend that you can persevere?
By pausing the business, you can focus your energy on generating cash through a job or an Obama O, without the negative emotions that come from permanently closing down.

Pivoting your business might be a good idea – if there’s a new market, new products and services or a new partnership opportunity on your doorstep, why not test it out?
By pivoting the business, you can keep the essence of your brand alive while also tapping into the most lucrative opportunities.

Persevering with your business might be a good idea – if there’s a light at the end of the tunnel and you know you’re well positioned to serve your customers in 2021.
By persevering, you can keep your team employed and work on the high value growth preparation projects that you’d previously neglected.

All three are worth considering, please don’t let fear take one of them off the table.
Once you’ve made a well thought out decision, there’s a natural set of steps for how to do each of them well.
What gets people stuck is the second-guessing, constantly agonising over whether they should have picked a different path.

Do you have an aversion to paid customer acquisition?
Growth is a huge priority for most businesses right now, either the regain lost ground, or to make the most of the current upheaval.
An interesting theme I’ve seen is an aversion to paid customer acquisition.
It takes a while to verbalise, but there are a lot of entrepreneurs with a resistance to spending money on social media or search engine marketing.
When I ask about it, there’s not a clear answer, so I’ll take a guess.

1. You don’t think paid customer acquisition works.
Except…of course it works.
You’ve been acquired as a customer by other businesses ten times this year, even if you don’t realise it.
You could definitely use today’s tools and platforms to get in front of customers who would love your brand.

2. You don’t think paid customer acquisition is worth the money.
I get this one, we tell ourselves that there’s no margin for marketing costs, but the maths is pretty compelling.
Spending money to acquire customers earns you more money than it costs, if you know what you’re doing.
They say social media marketing is an incredible way of turning 10c into $1 over and over again, or a great way to turn $1 into 10c.
I’d suggest trying the “Yes If” approach rather than making assumptions, e.g. “I’d do it if we could turn a $200 spend into $900 of extra revenue”.

3. You think it sounds cool to one day say “Oh we don’t spend any money on advertising”.
This might hit a bit close to home, but I hear it a lot and I used to think it was cool too.
Essentially it’s a brag, and a brag is a pretty bad reason to not take up opportunities to strengthen your business.
My recommendation is the same; can you look into your options or talk to other entrepreneurs who use paid acquisition tools?
Make whatever decision you like, once you’ve given it a fair assessment.

Where do you find a running mate?
A lot of entrepreneurs are in need of a new team member, but perhaps not the team member they first imagined.
Initially, the temptation is to bring in a salesperson, and sometimes they need an administrator to free up their time.
When we go digging, more often than not, they’re actually looking for a running mate.
Running mates are different to your typical team member – they’re co-conspirators, trusted advisors, people with skin in the game.
You can trust their judgement, dream and scheme about the future, even talk on the weekends.
Personally speaking, I can’t think of a scaled-up business where a founder doesn’t have one or two running mates.
The big question is, where might you find one?

For your field, are these people found or made?
Are they already working for you?
Are they running a different business, even in a different industry?
My suggestion is to start thinking about potential running mates long before you need one.
If they take a while to identify, interview and train, you can start meeting up with people before you are sure where their salary might come from.

If you had a cloning machine…
“But Isaac, I can’t think of who my running mate might be”
Here’s my suggestion – if you had a cloning machine, and could clone two real people who you know of, which two people would you pick?
Michelle Obama?
Your cousin?
Yourself?
Your friend’s running mate?

For these two people, what traits of their do you admire in particular?
Is it their work ethic?
Their creativity?
The types of assets they create?
The honest conversations they have with you?
Their grace under pressure?
Their attention to detail?
Their big picture thinking?

What I often find is that people rapidly know who they’d clone, and they often pick people outside of their industry.
One person even said they’d clone the receptionist from a local hotel, since they had such notable customer service skills and a great energy about them.
I might not actually have a cloning machine, but it’s a helpful thought experiment.

Social Media Paralysis
Pretty much every business needs to have an opinion over which social media platforms they need to take seriously.
For new businesses, most of the content is created by the founder – they generate the ideas, take the photos, use Canva and schedule all posts by themselves.
If social media is a growth engine, then these tasks become very sensitive, and the founder might be reluctant to hand the login details to anyone else.

Here’s the interesting bit: at first they all say it’s for “quality control”, but the real reason is the fear of being disliked.
They tell themselves that a single upset comment or negative review will completely tank their business – everyone will see it and assume it to be true.
This is, of course, bullshit generated by your brain to keep you safe.
We tell ourselves that our job on social media is to be liked by everyone, all the time.

Except…that’s an awful job when you put it like that.
Nobody can actually be liked by everyone, and those who try to do so end up being too bland or too try-hard.
Fear of being disliked makes us hesitant to create anything, second guessing every idea, and feeling a nervous dread at every notification.

The solution isn’t to be careless, nor should you give up altogether.
Neil Strauss recommends three waves of editing:
“The first draft is for you, the second for the reader.
The third draft, and a lot of people don’t do this, is for the hater.”I like this approach – first you make sure that you like the content, then you see if you can make it even better for your audience.
The extra step is to scan for anything that makes you an easy target for criticism – a poorly chosen quote, something that sounds bad out of context, promises and claims that are easily disproved, etc.
This removes the clumsy elements that attract criticism, but then you have to click Publish before your brain can trick you out of it.
You will get criticism, you will have people dislike you, you won’t be everyone’s cup of tea.
Once you’ve checked that a reasonable person would see your good intentions, you accept that you’re not everyone’s cup of tea but you’ve done what you could.
Other people’s opinions of your business are not your business.
Make sensible edits, control what you can control, don’t pretend you can magically please everyone.

Your brand needs a style guide
If you expect your team to be able to create content that you’d approve of, then you owe them a style guide.
A style guide is a set of rules for your brand, and as Marten Ascenzo says, restriction frees you from shitty design.
If you’ve ever had a designer work with you on your brand, they probably created a template for you to follow, but you can also make your own.
For example, a style guide would describe the colours, fonts, images, layouts and logos that make a piece of content look like “yours”.
A great way of identifying what works is to look at your best reports, presentations, posters and online content, and see what they have in common.
You can use these as reference points with your team – if you can show them three examples of high quality proposals, you massively increase the chances that they’ll create future proposals in a style you’re likely to approve.
There is a catch – you’re likely to spend a while overthinking every font and colour choice, at which point all options will feel equally flawed.
Fortunately, you aren’t the judge of your branding, since you aren’t your audience.
It doesn’t have to be perfect, it just has to be good, and it will save you from second-guessing every piece of work that your team produces.

Can we build a prototype in the next four weeks?
Amidst all of the current upheaval, the vast majority of entrepreneurs are actively designing new projects.
Some of them are at the start of the idea stage, some are deep into the idea stage.
What they need is a prototype, and luckily, you can still create decent prototypes while in lockdown.
Can you create an informative prototype in the next four weeks?
It doesn’t have to be a miniature version of the finished product, and it doesn’t even need to be a working prototype – it just has to answer your most pressing questions.

These questions include:

· How much do I enjoy this field? How much do I enjoy using these tools and platforms? Is there interest from paying customers?

· Is there interest from end users or beneficiaries?

· What questions do customers ask? What features do they hint might be dealbreakers?

· Could we combine two different ideas together? Is my initial idea actually two different ideas that are better separately?

· Which aspects are disproportionately valuable?

· Which aspects are disproportionately difficult?

Here are some examples of prototypes that can begin to answer these questions:

· Starting an Instagram page with your sample content

· Creating a Google form

· Building a landing page with your Value Proposition and a Call To Action

· Starting a blog that could become the basis of a book

· Creating a YouTube channel that could become the basis of an online course

· Starting a podcast that could become the basis of a recurring event

· Creating a mock-up for an app or piece of software

· Making a paper prototype of a physical product

· Designing an empty box to test with customers

· Storyboarding a user experience for a service

What’s wonderful about the above prototypes is that they bring ideas to life, and they let you experience exciting momentum…or the lack thereof.
e.g. you might record 5 podcast episodes or a few videos and become more enthusiastic than ever before, or the novelty might wear off.
Either way, great!
The ideation stage is fun, but only when interspersed with prototyping and real-world feedback.

Where are you winning?
I love this question – every single time it gets met with a long pause and a great answer.
Six months into lockdown, and everyone I talk to has had a few interesting wins, albeit overshadowed by all their difficulties.
The aim isn’t to be delusionally cheery, but rather to acknowledge that their assets and options have changed for the better as well as for the worse.
It might be a new team member who has really found their feet, or a new skill they’ve learned, or perhaps their web traffic has doubled.
Perhaps something that was once difficult can now be done on autopilot, or they’ve discovered some hidden passions through their recent soul-searching.
Either way, the mindset shift from “everything is terrible” to “some things are terrible” has a decent effect on our outlook.

Spend the time to get comfortable with proposals
I can’t believe we don’t talk more about proposal writing.
As a business goes from startup to established brand, it will be invited to take on larger and larger customers – such as wholesale customers, bespoke orders, partnerships, overseas stockists, consortiums who are pitching for a large tender, etc.
In these scenarios, a business owner is invited to quote a new offer, with new terms, at a new price point.
This is incredibly confronting – what numbers are you supposed to use?
Do you put your prices higher or lower?
What is a reasonable timeframe for delivery?
Who has the right to terminate the deal, and under what circumstances?
How will disputes or delays be handled?

I am staggered that this isn’t an essential part of business education.
It’s so tempting to leave money on the table, or to set the wrong expectations, or worse still to back away from the deal altogether.
I highly, highly recommend that business owners spend the time researching how people in their industry write and adjust proposals.
The details will vary by country and by field, but I bet there are mentors out there who can show you what they include in their proposals.
This will earn you more margin on each deal, remove the landmines that will blow up further down the track, and make it easy for either party to leave the arrangement on good terms.
Here’s the kicker – if you’re doing it right, you won’t be winning all of the proposals you submit.
If every possible customer thinks you’re cheap, you’re probably too cheap.
By becoming comfortable with submitting proposals, you’ll end up with more margin from fewer projects.

Battery Management
I’ve felt an interesting shift within myself in the last few months, and I see it mirrored in my clients.
There hasn’t been too much “new bad news” if that makes sense – the bad news is more of the same bad news.
e.g. extended lockdowns, more businesses going under, steady case numbers, long roads to recovery, more posts on deteriorating mental health, rising unemployment, etc.
What’s changing is my “battery”, the amount of mental, emotional and physical energy I have available each day.
I’d describe it as a 1% reduction each day; if I start today on 63% battery, then tomorrow might start on 62%.
You can get a lot done on 62% battery, but it’s noticeably less than what you could do last year.
I don’t mention this for sympathy, but to name it as a new priority for my work and personal life.
Our brains are processing stress at an unusually fast rate, so we can’t be surprised that it’s taking a toll.
I have needed to be more deliberate in reducing the things that drain my battery, prioritise the things that recharge my battery, and seek out downtime to increase my battery’s capacity.
Doing less can feel like failure, but in the long run I can’t out-hustle a leaking battery.

It turns out, a lot of people resonate with the analogy.
They still get a lot done, they still have highs and lows, but there’s less energy to divvy up amongst our usual tasks – let alone the surprises.
My situation is a work in progress, I don’t have a proven solution, but the language might help you articulate your own situation more clearly.
Your battery is important, you are important.
There’s no point in being a martyr, short term selflessness isn’t worthwhile if it’s going to burn you out.
We need kind people with healthy batteries.

“My problem is…no there’s no problem”
Someone said this in a recent session and it really made me laugh.
It was a sudden U-turn, a moment where they saw their situation in a new light.
You realise that the issues that feel big in your mind are actually non-existent, so you breathe a sigh of relief and have a good laugh at yourself.
I’m looking forward to more moments like these.

How might we get you a pay raise?
People have been surprised by this question, but it’s a good one in times like these.
I see business owners who are working harder than ever, growing their sales and adding new wings to their company all while trying to keep cash in the bank.
A pay raise might feel out of the question today, so let’s brainstorm some “Yes if…” scenarios:

· Yes if we double our number of large contracts

· Yes if we also give the rest of the team a raise

· Yes if I’ve taken on a larger role

· Yes if we have set aside six months’ worth of costs

· Yes if I reduce our costs by 5%

If you were employing a business manager, and the organisation they oversaw tripled in order volume, surely you’d see it as fair to give them a raise.
Why is it so different when the manager is you?
Inflation erodes your income by a few percent per year anyway, so no raise is essentially a pay decrease.
Have a think about it – what conditions would make a raise feel like a win for everyone?

I’ll be posting more coaching notes in a few weeks.
As always, please fill in a contact form if you’d like to work with me in the coming months.