How To Onboard New Hires The Right Way (James Dooley Interviews Mads Singers)
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What Does “How To Onboard New Hires The Right Way (James Dooley Interviews Mads Singers)” Talk About?
In this episode of the James Dooley Podcast, James Dooley sits down with management expert Mads Singers to explore the often-overlooked process of onboarding new employees. The conversation focuses on why so many smaller businesses fail to set new hires up for success from day one, and what practical steps can be taken to change that. Mads walks through a structured approach that begins before the employee even starts, covering the importance of having contracts, paperwork, and system logins ready in advance so new hires feel welcomed and valued rather than disorganized and overlooked.
The episode digs into one of the most critical and commonly neglected aspects of onboarding: setting clear, measurable goals for the first three months. Mads explains how defining what success looks like at the end of month one, month two, and month three gives both the manager and the new hire a shared understanding of performance expectations. The discussion also tackles the uncomfortable reality of knowing when a hire is not working out, with Mads sharing candid experience about the cost of holding onto underperforming staff too long, particularly in sales roles where results are measurable and the pattern is almost always clear by the three-month mark.
“Most people have no idea if they're winning or failing because the goals aren't clear.”
— Mads Singers
Who Are the Guests on “How To Onboard New Hires The Right Way (James Dooley Interviews Mads Singers)”?
Mads Singers is a management consultant and business coach with extensive experience helping business owners build high-performing teams. He specializes in people management, team structure, and operational efficiency, and is known for delivering practical, no-nonsense advice drawn from real-world experience scaling businesses. Mads has worked with entrepreneurs and smaller company owners in particular, helping them avoid common hiring and management mistakes that stall growth.
James Dooley is the host of the James Dooley Podcast and an entrepreneur with a background in digital marketing and business building. Known for his straightforward interviewing style, James draws out actionable insights from his guests by asking the questions that business owners and managers genuinely face day to day. In this episode, his question about micromanaging KPIs and how to break down goals by day, week, or month prompts one of the most useful parts of the conversation.
What Are the Key Takeaways From “How To Onboard New Hires The Right Way (James Dooley Interviews Mads Singers)”?
Here are the key points discussed in this episode:
- Preparing contracts, paperwork, and system logins before a new hire's first day sets a professional tone and signals that the company respects their time and excitement.
- Setting clear, milestone-based goals for the end of months one, two, and three gives both managers and employees a shared benchmark for measuring success.
- New hires who know exactly what targets they need to hit can self-assess their own performance, which builds confidence and motivation when they are succeeding.
- Having meaningful, prepared work ready for a new hire from day one prevents the disengagement that comes from feeling idle or unimportant in the early stages.
- Holding onto underperforming hires beyond the three-month mark, especially in sales roles, almost always leads to regret, and recognising this pattern early saves significant time and money.
“If I'm paying someone five grand a month, by three months they should make me more than that. Ideally fifteen grand to justify the hire.”
— Mads Singers
Is “How To Onboard New Hires The Right Way (James Dooley Interviews Mads Singers)” Worth Listening To?
This episode is worth listening to because it cuts through vague management theory and delivers a concrete, step-by-step onboarding framework that any business owner can apply immediately. Mads Singers speaks from genuine experience, including the uncomfortable admission that he personally held onto underperforming hires for too long because of sunk training costs, which makes the advice feel honest and grounded rather than idealistic. The three-month goal-setting structure he outlines is simple enough to implement in a small business yet sophisticated enough to create real accountability.
What makes this episode especially valuable is the dual perspective it brings to onboarding. Mads consistently frames every recommendation from both the manager's point of view and the new hire's point of view, which is rare and insightful. Understanding that a new employee needs to feel important, needs login access on day one, and needs to know whether they are winning or failing transforms onboarding from an administrative chore into a strategic tool for retention and performance. Whether you have hired one person or fifty, this episode offers reminders and frameworks that are easy to put into practice.
Who Should Listen to “How To Onboard New Hires The Right Way (James Dooley Interviews Mads Singers)”?
This episode is ideal for:
- Small business owners who are hiring their first or early employees and need a clear onboarding process to follow.
- Team managers and HR leads in growing companies who want to reduce early staff turnover and improve new hire performance.
- Entrepreneurs who have experienced the pain of a bad hire and want to build better accountability structures from the start.
- Sales team managers looking for a concrete framework for setting measurable targets and knowing when to act on underperformance.
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What Are Listeners Saying About This Episode?
“The point about having logins and system access ready before someone starts sounds obvious but I had never thought of it from the new hire's perspective before. Mads framing it as making someone feel important and like they matter completely changed how I think about our onboarding process. Really practical episode.”
“The three-month goal breakdown is something I'm implementing straight away. I've had sales hires where I genuinely didn't know if they were doing well until six months in, which is exactly the problem Mads describes. The advice about defining success before someone starts is gold.”
“I appreciated how honest Mads was about holding onto people too long because of training investment. That throwing good money after bad line hit home for me. Short episode but genuinely useful, especially for anyone running a smaller team without a dedicated HR department.”
**James Dooley:** Hi, today I’m joined with Mads Singers and today’s episode is about how to effectively onboard new hires. **Mads Singers:** Yep, and it’s a great topic and it’s a place where many, particularly smaller business owners, often leave a lot to be desired. So a simple process for how to onboard new people. When you’re onboarding people, there’s a bunch of things to take into account. You have paperwork, contracts and things like that. Get it sorted out. If you haven’t done it before they start, at least do it as the first thing when someone starts so that’s out of the way. Second thing is logins and access levels. As much of that as you can sort out before someone starts, the better. There’s nothing worse than being new in a company and every time you try to do something, you don’t have access or the right login. It feels unprofessional. When someone gets a new job, they’re excited. People want to feel important and like they matter. Sorting this in advance makes a huge difference. Think carefully about what access they need and set it up properly. Next is clear goals. In many smaller companies, staff are onboarded with no obvious goals or targets. People work for months and nobody really knows if they’re doing well or not. What you want to do is set goals for the first three months. By the end of month one, what should they achieve. By month two, what’s expected. By month three, what does success look like. **James Dooley:** Sorry, go on. **Mads Singers:** It’s important because as a manager you want to ask yourself, is this person a success or not. Even more important, the new person needs to know if they’re a success. If someone starts in sales and knows the goal is ten sales in month one and they hit twelve, they know they’re doing a great job. Most people have no idea if they’re winning or failing because the goals aren’t clear. From a management perspective, if someone isn’t right, knowing that after one month saves a lot of pain. Clear expectations benefit both sides. The last thing is making sure they have something meaningful to do from day one. Have work ready. Have something prepared. New hires want to get stuck in and contribute straight away. **James Dooley:** When you’re onboarding and setting KPIs and goals, how do you break them down. Is it day by day, week by week, or do you wait until the end of the month? How much do you micromanage expectations? **Mads Singers:** It depends on the role. If it’s a sales role and you already have a team, you usually know what success looks like. For a brand new role, I look at impact. What does this person need to achieve in three months for me to feel good about the hire. If I’m paying someone five grand a month, by three months they should make me more than that. Ideally fifteen grand to justify the hire. I set goals based on impact. Some roles are harder, like graphic design, where output is more subjective, but you can usually define projects or deliverables. We’ve had project roles where people missed deadlines but owned it and took responsibility, so we continued. But in most cases, when people don’t hit goals and we keep them on, we regret it. For sales roles especially, if someone hasn’t hit targets after three months, 99 percent of the time we regret keeping them. I used to hold on too long because we’d invested time and training, but throwing good money after bad is not how you win in business. **James Dooley:** For anyone watching, is there anything Mads has missed about onboarding new hires? What have you found important as you’ve grown teams? Let us know in the comments. Mads, I appreciate it. Thank you very much. Great chat again.
Creators & Guests
Host
James Dooley is a UK entrepreneur.