Mastering Deep Work and Authentic Sales: Game-Changing Insights for Fractional Executives

In a recent conversation with business coach Kay Phillips, we dove deep into strategies that can transform how fractional experts manage their time, set goals, and sell their services without feeling slimy. After building both bookkeeping and fractional HR businesses before transitioning to coaching, Kay brings a wealth of practical insights on how to work smarter, not harder.

The Deep Work Challenge: Overcoming "Attention Deficit, Ooh Shiny"

One of the biggest challenges for fractional executives is managing distraction. Kay points out that creative, ambitious people with the risk tolerance to start their own businesses often struggle with what she humorously calls "attention deficit, ooh shiny" or ADOS.

"Distractions are part of it, but it's the distractions that you think are actually work that tend to keep people stuck," Kay explains. "I call it pre-crastination. You feel like you're doing something productive and you're being busy, but that's all you're doing—you're busy being busy."

These "productive distractions" might include falling down YouTube learning rabbit holes, starting newsletters, increasing social media presence, or building communities. While these activities feel like work, they're often long-term strategies that distract from immediate revenue-generating activities.

Identifying Real Work vs. Busy Work

How do you determine what constitutes real, productive work versus busy work? Kay recommends using the Eisenhower Matrix to categorize tasks based on importance and urgency:

"It's either important and urgent, important but not urgent, urgent but not important, or neither," she explains. "The important and urgent square is where everyone tends to put everything. But unless there is a very real consequence or deadline, that box is almost entirely empty for most people."

Real deadlines with consequences—like picking up your child from school or delivering on client promises—belong in the important and urgent category. But many tasks that feel urgent, like clearing out your inbox, probably don't.

The Power of Deep Work and Boredom

Kay advocates for focused deep work time, noting that research shows most people are truly productive for only about four hours daily. The key is making these hours count through intentional focus.

One surprisingly powerful strategy is embracing boredom. "Our grandparents and beyond were really able to harness boredom in good ways," Kay notes. "If you read older books, people spend a lot of time just sitting around doing nothing, staring at a fire."

This seemingly unproductive time allows your subconscious to work through problems while your ego steps aside. In today's world of constant notifications and distractions, deliberately creating space for boredom can lead to unexpected breakthroughs.

Systems Over Goals: A Fresh Approach to Achievement

When it comes to achieving results, Kay suggests a shift in thinking from setting goals to designing systems:

"We have an action problem, not an information problem," Kay explains. "It's what you're doing on an hourly, daily, weekly basis that is going to get you to a goal."

Rather than focusing solely on targets, create systems and habits that make achievement almost inevitable. The analogy Kay uses is that most people know what to do to get six-pack abs—the information is readily available. What's missing is consistent action and proper systems.

"Make it so easy that it's just what you do," she recommends. "You almost don't have a choice. It's like an autopilot."

This approach echoes the experience many of us have had with habits like flossing—initially challenging but eventually automatic after consistent practice. The key is creating a system you can stick with until it becomes second nature.

Authentic Sales in an AI-Driven World

In today's environment where AI-generated outreach is increasingly common, authentic human connection becomes even more valuable. Kay predicts "a return to very focused, very clear, kind of messy almost" communication like personal videos, phone calls, and old-school networking.

"AI has never bought anything from me, and I don't anticipate an AI bot will ever buy coaching from me," Kay points out. This necessitates what she calls "H to H" (human to human) connection rather than just B2B or B2C.

For fractional executives concerned about coming across as inauthentic or "salesy," Kay recommends approaching sales as a form of service rather than persuasion:

"Nobody wants to be sold on anything. People aren't just going around looking for ways to spend money. They want solutions for a reason, and they might not know that reason until you help them."

She suggests using genuine curiosity to help potential clients recognize problems they've normalized. "We all normalize our pain," she notes. By asking thoughtful questions and truly listening, you can help them understand how much better things could be—without any traditional "pitching."

Practical Implementation: Action Steps for Fractional Executives

To apply these insights to your fractional business, consider these practical steps:

1. Create a deep work system: Block out dedicated time for your most important work. As Kay puts it, "If you don't plan ahead of what you're going to accomplish in that block of deep work, it's literally useless." Remove distractions by using blocker apps and setting clear objectives.
2. Start small with habits: Begin with just 10 minutes of the thing you're avoiding. "I'm already in it this deep, I might as well keep going," is a mindset Kay uses to build momentum.
3. Gamify difficult tasks: Set timers, create challenges, or build reward systems to make deep work more engaging. Kay explains, "That's really big in the ADHD community especially, to try to gamify it."
4. Embrace strategic boredom: Schedule time to simply sit and think without devices. Let thoughts come and go without immediately acting on them.
5. Design systems, not just goals: Create daily routines that automatically move you toward your objectives. Focus on making these routines so simple they become automatic.
6. Use AI strategically: Leverage tools like ChatGPT for research, feedback, and efficiency, but maintain authentic human connections. As Kay recommends, "When you approach selling more as serving, that's where you're gonna find you just get sales really easy."
7. Personalize your outreach: Consider using video messages to stand out in a sea of automated communications. "I've found sending a quick Loom video... helps people see like, this is a legit person," Kay shares.

The Path Forward: Consistency and Authenticity

The consistent theme throughout these strategies is balancing efficiency with humanity. As Kay puts it, "It's simple, not easy." The concepts themselves are straightforward, but implementation requires consistency and the right mindset.

Remember that you started your fractional business for flexibility and autonomy. Give yourself permission to work in ways that suit you best, whether that means finishing your deep work by noon or taking afternoons off occasionally.

The future belongs to fractional experts who can harness technology while maintaining authentic relationships. By creating systems for deep work, embracing strategic boredom, and focusing on genuine human connection in your sales process, you'll build a more sustainable and fulfilling business.

As Kay reminds us, "The things you do every day are gonna be what get you somewhere. Make sure those things that you're doing are gonna lead you to where you actually want to go."

Mylance

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