The Shortcut to Painless Hiring
Four things to get straight before you post the job, so you hire for the problem and not the title.
By Laura Little
I originally wrote The Shortcut to Painless Hiring for Paul Ogonowski's newsletter, The Anti-Grind SaaS Manual. I see the same hiring mistakes across founder-led businesses: a job title gets decided before the problem is understood, a role becomes three jobs in one, or the requirements change the moment someone likeable walks into the interview.
Paul added his perspective as a founder, and we collaborated on a free Claude skill to help you work out whether you need to hire at all. I built the prompt around the questions I ask businesses; Paul turned it into a skill your AI can run. I’ve kept links to his resources below. And if you’re looking for a Head of Growth, you’ll find a way to connect with him at the end.
You can find his newsletter at The Anti-Grind SaaS Manual. His related piece, Don’t Hire Yet, is a useful companion to the first tip.
If the thought of making a new hire has got you stressed to the max you aren’t alone. Hiring can be an absolute cluster.
While the theory of hiring does not seem that complicated, create a role, post it, screen, interview, make an offer, the reality of the hiring process if not done strategically, can be stressful, expensive, and eat into your most valuable asset which is… time.
And what is time to a business? It’s Money.
Working with founders I’ve heard things like “it was a dumpster fire”, “huge mistake”,
“We hired our first employee and it was the worst decision ever”
“This employee has added more costs, time consumption, and issues than it’s brought revenue”
But guess what, for those of you that are hiring without the help of a talent partner or in-house talent manager, you can save yourself the headache by following some of my quick tips to easier hiring.
Tip 1: Dig into your business pain, find your why
When you start with these questions, you’ll get more clarity on what you really need.
- What business problem/s is this hire supposed to solve
- Is this problem recurring or fixed?
- Could this problem be solved with software?
Not every problem requires a full time solution, some problems can be solved with a short term contract, some can be solved over time with a fractional provider, and then some can also be solved with software.
For example, let’s say your team is spending hours every week manually scheduling customers, following up on appointments and fixing booking mistakes. Your first instinct might be, “I need an admin person.” But when you look at the problem, you may discover that what you really have is a broken scheduling process that could be solved with an operations audit.
Alternatively, you might discover that the work genuinely requires a human, but only for 10 hours a week. Now you’re looking for a contractor or part-time hire, not a full-time employee.
When you skip this step, you can end up hiring a perfectly capable person into a role destined to fail. And now you’re paying a salary while still dealing with the original problem.
Paul Ogonowski and I collaborated on a free Claude skill to help you work through this. I created the prompt, and Paul turned it into a skill your AI can run on your business.
It asks eight questions, one at a time, then helps you identify whether the best fit is a better process, software, a flexible human (contractor, fractional or part-time), a full-time hire, or a combination. If a hire is the right answer, it also drafts outcomes for day 90, six months and a year, plus three screening questions based on your business problem. Grab the skill we made here.
If this hits home, send it to a founder who’s about to make a hire.
Tip 2: Build the role around the problem, not a job title or description
The foundation of hiring strategy is to identify the problem before you push the button on the process, and THEN you need to confirm that the problems fall inside the same jurisdiction of domain expertise.
What do I mean by that? Well a bricklayer can be an expert in brick laying, and maybe in a pinch help dig a hole for plumbing, but would you ask him to do a complete bathroom installation? Probably not right? It falls outside of his domain expertise.
This is a common problem, where a role gets stuffed with so many varying skills and tasks that it becomes impossible to find the right person because no one could possibly fulfill the role as written or described.
This can also happen when businesses are trying to turn what could be a contract role into a full time role, in order to justify the hire, and inadvertently create additional responsibilities to “fill time”. If you’re unsure always revert back to the questions we’re asking, what business problem/s do I want this hire to solve.
As you build your role description, also reflect on what should have changed for the business at day 90, 6 months and one year.
Is it improved operational process? Is it increased revenue? Is it more visibility?
Know an owner who’s about to post a job ad this month? Send them this before they hit publish.
Tip 3: Screen for evidence, not keywords
Let’s talk about the resume screening and all it’s failings. Because let’s be honest even on a good day it is impossible to know “that much” from two pieces of paper stuffed to the brim with key words and sentences that none of us know what they mean.
Sometimes I see resumes that I’ve read 10 times and I still don’t know what the candidate did.
It was hard to begin with, it’s even harder now. Since the arrival of AI every candidate has the opportunity to create a perfect resume, that matches perfectly with your role.
Here’s how you can beat the AI out of the resume, and screen for fact not fiction.
Include scenario-based questions in your application screening questions. This is an opportunity to ask questions that are specific to your business. Use this to your advantage.
To create the questions for screening, think of 3 current problems that you would like them to solve in their first 90 days of employment. Each question should be specific and ideally give the candidate the opportunity to show you how they think, how they executed, and what the result was.
Remember as you create these questions and your job description, you’re consistently asking and reflecting on,
Does this person understand my business problem?
Has this person fixed this exact problem that I’m having? (adjacency is ok)
Can this person continue to solve future problems in their domain of expertise
I recommend you divide the questions into, “what would you do” “what have you done” and a high stakes “working style” response related question.
Here are some hypothetical, business scenarios and corresponding screening questions:
The What Would You Do:
The business is a general contracting company with a focus on Kitchen Installations. Material pricing has been inconsistent and they’re sure they’re losing revenue because of material cost fluctuation which is making it difficult to accurately estimate the cost of a kitchen that’s ordered in July, but installed in October.
Candidate Screening Question: Material costs for kitchen installations are changing frequently, but our estimating process still relies on historical or inconsistent pricing making it difficult for us to accurately predict our cost and revenue.
How would you approach this problem? What information would you want to understand first? What would you investigate, and how would you determine where we’re losing margin? Once you understood the cause, what would you change?
Notice how we’re focused on putting the candidate inside our business problem and discovering how they think.
An example of the “What have you done”
The Business Problem: You are a cleaning company that services offices and local businesses. You want to increase customer acquisition through a first-time sales hire, but don’t know where to start.
The Candidate Question:
Tell me about a time you joined or worked with a business that needed to increase customer acquisition but didn’t yet have a clear or established sales process. How did you assess what was needed, what did you put in place, and what was the outcome?
An example of the “Working style and values”
For this one think about a high stakes scenario in your business where the most pressure lies. Create a question that gives the candidate an opportunity to express their working and response style.
The Business Problem: You run a website design company working toward an important client launch. A junior member of the team forgets to order something required for the project, and the mistake sets the whole team back by a week.
The Candidate Question: Tell me about a time a team member made a mistake that affected a deadline or created additional work for the team. How did you handle the situation with them, what did you do to get things back on track, and what happened afterward?
If you’ve ever hired the wrong person for the right reasons, share this so the next owner doesn’t.
Tip 4: Invest in the process
Making a hire is one of the biggest investments you can make in your business, so take the time to be thorough and do the pre-work that goes along with it. It will save you time, resources and money later.
Remember, you’re investing in talent over the long term. You’re hiring someone who can continue to add value as the business changes and grows over the next 3–4 years.
As you move into the interview phase, prepare a set of core questions that you ask every candidate. Consistency is important here! If everyone is being assessed against completely different questions, it becomes really challenging to compare candidates accurately and stay focused on what you’re screening for.
I also like to use an interview recording tool so I can go back to what was said rather than relying on memory, or my handwriting! Just remember to ask for consent before you start recording.
The goal here isn’t to turn yourself into a recruiter. It’s to create enough structure that you’re making a considered business decision instead of hiring based on urgency, instinct, or whether you happened to like someone in an interview.
Before you start interviewing, decide what evidence you need to see. Go back to the original problems you identified at the beginning of the process and ask yourself: Has this person actually demonstrated that they can solve them?
And try not to move the goalposts halfway through.
One of the easiest things to do in hiring is meet somebody you really like and suddenly decide that three of your original requirements weren’t that important after all (Paul wrote about this here).
Sometimes requirements should change because you’ve learned something during the search. That’s okay. Just make sure you’re changing them because the business problem has become clearer, not because you’re trying to make a candidate fit.
Hiring will never be completely painless. You’re making a significant decision about a person you don’t know particularly well, based on a limited amount of information, and hoping they’ll become an important part of your business.
Remember to start with the problem. Build the role around that problem. Screen for evidence that the person can solve it. Then give the hiring process the same attention you would give any other significant investment in your business.
Because painless hiring isn’t about finding candidates faster. It’s about knowing exactly what and who you need before you start looking.
That’s the shortcut to less painful hiring.
Work with Paul Ogonowski
Paul publishes The Anti-Grind SaaS Manual for B2B SaaS founders who can’t be the whole GTM anymore: practical playbooks and the stories behind them. Systems over hustle. Fun over grind.
- Grab his skills and playbooks. Claude skills and printable playbooks from his newsletter, all in one place. Open The Skill Vault →
- Explore his founding membership. The original edition included an annual 60-minute GTM teardown to identify where growth still depends on you and what to hand off first. See membership details →
- Hire Paul as your Head of Growth. In the original edition, Paul shared that he was looking for his next full-time role at a B2B SaaS company. Learn more and connect with Paul →
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