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Chapter 9: Building Your Dream Team: Hiring and Delegation Strategies
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“A team is not a group of people who work together. A team is a group of people who trust each other.”
Building a successful advisory practice isn’t just about scaling up or boosting efficiency. Sometimes, it’s about survival. In December 2018, my world turned upside down when my older sister had a sudden seizure while visiting Florida. She underwent two emergency brain surgeries and spent six months in the hospital relearning how to walk and talk. Only my dad and I could be there with her.
I essentially lost an entire busy tax season in 2019. That crisis forced me to confront a hard truth I’d been avoiding: I could not run this firm by myself. I had been so consumed by my business and family that I hadn’t noticed her steady decline in health. It wasn’t a brain tumor or cancer – the diagnosis was Wernicke-Korsakoff syndrome (a severe neurological condition, often caused by malnutrition).
While my sister lay in a hospital bed with feeding tubes and wrist guards on, I was scrambling to keep my business alive. The only reason I managed to do so was that I had already begun making substantial changes in how my practice operated – including starting to build a team.
Right in the middle of this personal storm, I received a Facebook message from Veronica. She had seen one of my CPE webinars and reached out to ask if I had any open positions because she loved what I was building.
I remember answering her from my sister’s hospital room. Within weeks, she became my firm’s tax manager – I call her my angel to this day. Veronica has since grown from tax manager to CFO, and now she serves as our Chief Tax Strategist at TaxPlanIQ. Her story is living proof that having a trustworthy team member at a critical time can save your business. It also reinforced why building a strong team matters more than any single strategy or system.
This chapter focuses on the process of hiring, training, and managing a team that aligns with your vision and values. We’ll explore how to identify which roles you need most, write job descriptions that attract the right candidates, and conduct interviews that go deeper than surface-level answers. We’ll also talk about the challenge of letting go – the mistakes I made early on and the leadership lessons that reshaped how I lead today.
Growing a team can feel daunting. The “no one can do it as well as I can” mindset is very real for entrepreneurs. But the fact is, you cannot build a seven-figure firm (and reclaim your time, aiming for something crazy like a 4-hour workweek) without a team you deeply trust. When you get it right, not only do you free yourself up, but you also amplify your firm’s ability to deliver amazing service. Your income and impact can grow exponentially once you’re not the only one doing all the work.
I made plenty of mistakes early on. For example, I once hired someone (okay, more than one) who looked perfect on paper – and I ignored some red flags, like rushed reference checks or a gut feeling that something was off. Within two weeks it was clear we were not aligned on values. One hire even refused to respect my final say as the owner; I dreaded our meetings. I had to let them go (and even had to block some harassing emails afterward). That experience taught me what every advisor eventually learns: skills can be trained, but values cannot. From then on, I started hiring for culture fit first, knowing technical skills could be developed if the person had the right attitude.
That doesn’t mean I stopped testing for skills altogether. My number one core value is honesty, and hiring taught me that people will sometimes tell you whatever they think you want to hear. One candidate confidently rated themselves “8 out of 10” in QuickBooks. So on a Zoom call, I shared a sample QuickBooks file and asked them to pull a basic Profit & Loss report.
They had no idea how. That ten-minute test saved me tens of thousands of dollars in what would have been a bad hire. Ever since, I include simple skill tests in interviews. And because we handle sensitive client data, I also began running background checks on new team members (services like Gusto make this easy to integrate into their automated payroll solution).
One of my earliest (and best) hires was Cheryl, who started as a contract bookkeeper. My firm was pretty chaotic back then, but Cheryl’s consistency and reliability brought much-needed stability. She eventually grew into our accounting manager. Looking back, my biggest regret with Cheryl was being too task-oriented and not spending enough time mentoring her or investing in her growth.
She still gave her best and even became a friend. When she eventually left to start her own firm, I was incredibly proud of her – but it reminded me that leadership is about elevating others, not just getting tasks done. In hindsight, I realize I could have groomed her for bigger roles within my firm. That experience reinforced that leadership isn’t about holding everything together yourself; it’s about finding people with integrity, loyalty, and dedication, then creating an environment where they can thrive alongside you.
Building your dream team is not optional if you want to achieve the Balanced Millionaire life – the kind of life where you have the time, freedom, and peace of mind to be present with your family when they need you most. Today, I have an exceptional team of over 20 at TaxPlanIQ. Realizing my own limitations in growing an eight-figure SaaS and wanting to reach as many tax advisors as possible, I stepped aside as CEO January 2024. It allowed me to finish my doctorate in leadership, write two books (yes, there’s another one coming for entrepreneurs!), and spend more time with my family. Let’s dive into how to actually get there.
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Why Building a Dream Team Matters
True success is not just about money. It is about building a sustainable, fulfilling practice that does not burn you out. A dream team makes that possible by giving you leverage:
Multiply Expertise: Bring in people whose strengths complement or exceed your own. Maybe you excel at tax strategy but struggle with details, or maybe marketing is not your thing. The right hires expand what your firm can deliver.
Increase Capacity: You can only serve so many clients alone. With a capable team, you handle more work and bigger opportunities without adding endless hours.
Boost Efficiency: Delegation means the right people do the right work. You are not spending $300 per hour owner-time on $30 per hour tasks. The result is faster, more cost-effective service.
Spark Innovation: A diverse team brings fresh perspectives. Different backgrounds lead to better ideas, process improvements, and creative solutions.
Build Culture: People thrive in a positive, collaborative environment. Strong culture keeps great employees and reassures clients that they are supported by an entire team, not just one overworked advisor.
The evidence is clear. Highly engaged teams consistently outperform solo operators. In high-trust workplaces, productivity and engagement jump dramatically compared to low-trust environments. A strong team is one of the best investments you can make in your practice and in your own well-being.
Identifying Roles and Responsibilities
The first step in building your team is deciding who you need and what they should do. Start by tracking your own tasks for a week or two and categorizing them. Common buckets include:
Administrative: scheduling, email management, data entry, billing, collections. These are important but not specialized and can be handled by an administrative assistant or office manager.
Bookkeeping/Accounting: reconciliations, financial reports, payroll. If you offer these services, a dedicated bookkeeper or accountant can take the bulk of this work.
Tax Preparation: gathering data, entering it into tax software, initial return prep. A tax preparer or junior accountant can handle these under your review. Personally, I retrained experienced staff as project managers for each client, which gave clients one point of contact and set clear response times.
Tax Planning/Advisory: researching law changes, modeling scenarios, drafting planning ideas, client meetings. You may start with this yourself, but eventually a junior advisor can help.
Marketing and Sales: social media, newsletters, prospect calls, webinars, lead follow-ups. This can often be a virtual assistant with marketing skills.
Technology/IT: managing your tech stack, troubleshooting, optimizing your website or client portal. Early on, you may outsource this to a consultant or rely on a tech-savvy team member.
The key is asking: which tasks should you keep, and which could someone else do better or cheaper? Also consider which roles directly add revenue (like a tax preparer) versus those that free up your time (like an admin). Both matter, but the right first hire is the one that relieves your biggest bottleneck.
Who Do You Hire First?
This is one of the top questions I hear. My answer: hire for your pain point.
If admin work is drowning you, hire an assistant. Even part-time help with scheduling, forms, and email can free 20 percent of your day.
If bookkeeping is slowing you down, hire a bookkeeper who can do it faster and more systematically.
If you are overwhelmed at tax season, bring in a tax preparer, even if seasonal or contract.
If you never have time for marketing, hire someone to keep your pipeline moving while you serve current clients.
Often the best first move is an admin hire. But if admin is under control and technical work is keeping you up at night, hire technical help first.
Also think about what drains your energy. If you hate a task, that is a great candidate to delegate. Not only will it make you happier, but someone else will probably do it better. Coaches or mentors can help you spot blind spots here. Once you know the role, define it clearly so that you and future candidates both know what success looks like.
Writing Compelling Job Descriptions
A good job description attracts the right people and filters out the wrong ones. Think of it as part clarity, part marketing. Include:
Title: clear and standard (Staff Accountant, Client Service Associate, Tax Planning Analyst).
Summary/Purpose: a short overview of what the role contributes to your firm.
Key Responsibilities: five to ten bullet points describing the actual work.
Qualifications: education, certifications, experience, plus any “nice-to-haves.”
Attributes: the personal qualities that fit your culture.
Culture and Values: your mission, vision, and why someone would want to work with you.
Compensation and Benefits: transparency helps. List a range or at least highlight perks like remote options or education support.
How to Apply: clear instructions, timelines, and even a small test of attention to detail.
Match the tone of the job posting to your firm’s style. A casual firm should not sound stiff, and a formal firm should not sound too casual. Referrals often bring the best hires, but they still need a clear description of what the job entails.
Conducting Effective Interviews
Once you have candidates, the interview process helps you separate the good from the great.
Prepare Questions: cover both skill and fit. Ask about experience, problem-solving, and work style.
Ask Behavioral Questions: “Tell me about a time when…” reveals how they acted in real situations.
Listen Actively: let them do most of the talking. Take notes and follow up.
Assess Culture Fit: skills can be taught, attitude cannot. Ask directly what environment they thrive in.
Be Honest About Challenges: share realities like busy season hours or everyone pitching in.
Check References and Skills: verify reliability and give a short practical test. For example, a bookkeeping reconciliation, a draft social post, or a technical tax question. Keep it reasonable in scope.
Use Your Core Values: ask questions tied to your values, like continuous learning or innovation. I recently asked a virtual assistant candidate how often they use AI and to give a time-savings example, because innovativeness is one of our firm’s values.
The goal is not just technical skill but someone who thrives in your firm. A strong cultural fit with adequate skills is often better than a technical expert with the wrong attitude. Trust your instincts and move quickly with a good candidate, because great people usually have options.
Identifying Roles and Responsibilities
The first step in building your team is figuring out who you need to hire and what exactly they will do. Start by looking at your own plate and categorizing tasks. A simple exercise is to jot down all the tasks you handle for a week and then bucket them. Common categories in an advisory firm include:
Administrative Tasks: Scheduling meetings, managing email, organizing files, billing, collections, and client inquiries.
Bookkeeping and Accounting Tasks: Bookkeeping, reconciliations, payroll, and financial reports.
Tax Preparation Tasks: Gathering client data, inputting into software, preparing returns, and drafting extensions. I once converted experienced staff into client project managers, making them the one-stop shop for every client request with clear response-time commitments.
Tax Planning and Advisory Tasks: Researching updates, modeling scenarios, and meeting with clients.
Marketing and Sales Tasks: Managing social media, writing newsletters, handling prospect inquiries, organizing webinars, and following up on leads.
Technical and IT Tasks: Managing your tech stack, troubleshooting software, and optimizing your client portal.
Once you have identified categories, ask yourself which tasks you should continue doing and which could be handled by someone else. Also consider which roles directly generate revenue and which free up your time indirectly.
Who Do I Hire First?
Hire for the role that most relieves your biggest bottleneck. If administrative work is consuming your time, bring in an assistant. If tax preparation is overwhelming, hire a preparer. If bookkeeping is slowing you down, hire a bookkeeper. If marketing is neglected, hire support for sales and pipeline building. Many solo practitioners find that hiring an administrative assistant is the most impactful first move, because it frees up a large amount of time. But if your real bottleneck is technical work, then start there.
Also consider what you dislike doing. Tasks that drain your energy are the best candidates to delegate, because someone else will likely do them better and enjoy them more. A coach or mentor can help you see blind spots in this process and clarify the best way to leverage your time. Once you have zeroed in on the role you need, write a clear description of what that person will do. Even if you are not an HR expert, clarity here is key for both you and your candidates.
Writing Compelling Job Descriptions
A job description is both a clarity exercise and a marketing tool for your firm’s vision and culture. Keep titles clear, summarize the role’s purpose, list responsibilities, outline qualifications, highlight desired attributes, describe your culture and values, share pay transparency if possible, and explain how to apply. Referrals can be your strongest source of staff, but even referred candidates need a job description so expectations are clear.
Conducting Effective Interviews
Resumes and cover letters only tell part of the story. Interviews reveal skill, fit, and attitude. Prepare questions in advance, including both technical and behavioral ones. Listen actively and assess cultural alignment. Be honest about challenges like workload during busy season. Always check references and include a short skills test. Incorporate your firm’s core values into your questions. For example, I ask virtual assistant candidates, “How often are you using AI? Give me a time-savings example.” This quickly shows if they share our value of innovation.
The best hires often have the right attitude and enough skills to grow. A poor cultural fit, no matter how technically sharp, can hurt your firm.
Leadership
You almost thought you’d make it through this chapter without leadership advice. Sorry friend, but I have a doctorate in leadership, and this is one of the hardest topics to preach and practice. Still, I would be remiss not to include it. After hiring and managing more than 100 people, here are the insights I gained through trial, error, and growth:
Care About People as People First: Early in my leadership journey, I was overly focused on efficiency and profitability. I learned the hard way, especially through my experience with Cheryl, that the most effective leaders prioritize relationships first. As Kim Scott explains in Radical Candor, “Care personally, challenge directly.” Leaders who genuinely care build loyalty, trust, and teams that outperform task-driven management alone.
Let Go and Trust: Perfectionism and fear of mistakes kept me micromanaging. Cheryl taught me what real delegation looks like. Trusting her expertise transformed both our relationship and the business. Trust empowers team members to take ownership, innovate, and excel.
Vulnerability Builds Strength: Brené Brown’s Dare to Lead emphasizes that trust and vulnerability go hand in hand. For too long, I believed showing vulnerability would undermine authority. The opposite was true. When I became more open about struggles and failures, my team grew stronger. Vulnerability invites collaboration and creates resilient leadership.
Hire for Core Values, Supported by EOS: The Entrepreneurial Operating System (EOS), outlined in Gino Wickman’s Traction, taught me to live by core values. These are no longer posters on the wall but the lens through which we make every hiring decision. Asking “Does this candidate embody our values?” has kept our team aligned and committed.
Right People, Right Seats: EOS also stresses having the right people in the right seats. Early on, I hesitated to let go of team members who were not thriving. Keeping them felt compassionate, but it actually hurt both them and the firm. Helping someone transition to a role or environment better suited for them is an act of clarity and kindness.
John Maxwell, in The High Road to Leadership, says leadership can be summed up in one word: “Others.” Leadership is not about us but about elevating those around us. These lessons reshaped how I scaled beyond myself and ultimately achieved the Balanced Millionaire lifestyle I desired. EOS gave me practical tools, but personal growth gave me the mindset shift. Together they showed me that building a dream team is not just good business, it is the only way forward.
You may not get it right every time. I did not. I made poor hires and kept them too long, but I also found amazing ones who took our firm to new heights. Every hire teaches you something about what your firm truly needs. One day, you will look around and realize you have that dream team—a group of people who not only deliver but also care deeply about the business and each other. When you reach that point, running the firm becomes a joy, and your clients will feel the difference.
All right, we have hired and built an awesome team. What is next? In Part 4 we will focus on you—managing your time and energy so you can fully achieve the balance and freedom that this effort is meant to create.
Action Items
Go to Jackie.CPA to complete these steps online and access templates, checklists, and bonuses.
Map work and pick your first hire. List everything you do for two weeks, split into “Only I can do” and “Someone else can own.” Convert that into a role profile and choose the first hire that relieves your biggest bottleneck.
Standardize your hiring system. Write the job description, add a 30–60-minute role-relevant skills test, and create a simple core-values rubric that you score in every interview. Save all three as reusable templates.
Design a 90-day onboarding plan with a scorecard. Define week-by-week training, three milestone reviews, and 3–5 KPIs for the role so success is obvious to you and the new hire.
Practice real delegation this month. Choose one task you have never delegated. Write a clear brief with the desired outcome, constraints, and deadline. Hand it off, review together, and document the process for next time.
Updated Endnotes
Simon Sinek – Start with Why (Portfolio, 2009). Reflects the idea that trust, not just working together, makes a team truly cohesive.
Paul J. Zak, “The Neuroscience of Trust,” Harvard Business Review (Jan 2017). Shows how trust improves productivity and engagement.
Gallup, State of the Global Workplace reports. Confirm that highly engaged teams outperform solo operators.
Kim Scott, Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity (2017). Core idea: care personally, challenge directly.
Brené Brown, Dare to Lead: Brave Work. Tough Conversations. Whole Hearts. (2018). Trust and vulnerability as leadership tools.
Jim Collins, Good to Great: Why Some Companies Make the Leap… and Others Don’t (HarperBusiness, 2001). Introduces “Level 5 leadership” and “right people, right seats” concepts.
Gary R. Collins, Christian Coaching: Helping Others Turn Potential into Reality, 2nd ed. (NavPress, 2009). A biblically grounded coaching model for leadership and personal growth.
John C. Maxwell, The High Road to Leadership (2022). Leadership defined by serving others.