Entrepreneurs are brilliant at solving everyone else’s problems, but often get stuck in their own because they won’t fully leverage support. In this episode, Shannon Waller chats with Terry Pham of Superpowers about the five biggest delegation roadblocks, how to build a true strategic partnership with your executive assistant, and why letting go is the fastest way to 10x your impact. Download Episode Transcript Show Notes: Entrepreneurs are great at getting other people unstuck but often need a mirror to see where they’re stuck in their own habits and identity. A truly great executive assistant (EA) is a strategic partner with a “heart of hospitality,” anticipating your needs and future points of friction so you can stay in your Unique Ability®. The best entrepreneur–EA partnerships treat each other as complements rather than clones, so strengths and weaknesses balance instead of compete. Powerful delegation starts by making space to work on the partnership, not just on the day-to-day tasks. Terry’s five delegation roadblocks—”It takes too much time,” “No one can do this like me,” “I didn’t know I could delegate this,” “I actually enjoy this,” and “I don’t believe I deserve support”—show up in almost every entrepreneurial business. “It takes too much time, so I’ll just do it myself” is usually a bad math problem where five-minute tasks, repeated all year, slowly add up to days of lost focus. You can dramatically speed up delegation by labeling tasks as “plastic balls” (low risk, your EA runs with it) or “glass balls” (high stakes, clear guardrails and check-ins), so your EA instantly knows how careful to be and how much initiative to take. Most entrepreneurs are long Kolbe Quick Starts who delegate big-picture outcomes, while most EAs are long Follow Thrus who want details, so clear language around risk and expectations protects both sides. “No one can do this like me” is only true for activities in your Unique Ability; everything else should be delegated so you can spend your best hours on the thinking, relationships, and creativity that actually grow the business. Have your EA map your task list into what energizes you versus what drains you, then target the Excellent and Competent activities for delegation first. Many entrepreneurs discover they only love 20 percent of a task and can happily hand the other 80 percent to their EA to prepare, organize, and follow through. “I didn’t know I could delegate this” is common for rugged individualists who’ve built unconscious competence and simply stopped seeing tasks that could be handed off. Ask your EA to track your invisible tasks for a week so you can see where you’re reflexively doing things that someone else could own permanently. You can delegate far more of your personal life than you think, from family dinners to social media, freeing energy for your biggest entrepreneurial goals. “I actually enjoy doing it” often hides a procrastination strategy where you choose familiar, low-stakes tasks like emails, meetings, and quick fixes over the strategic, uncomfortable work only you can do. Use the Eisenhower Matrix to keep yourself in the not-urgent-but-important work while your EA shields you from urgent-but-not-important noise. “I don’t believe I deserve support” is usually about ego or false humility and can stop entrepreneurs from fully using an EA even after they’ve hired one. Reframing support around impact, contribution, and your company’s bigger future makes it easier to receive help without getting stuck in self-judgment. If you love serving others but resist being served, remember you’re robbing someone else of the joy and pride of supporting you at a high level. Tools like Predictive Index and Terry’s Frequency Assessment help both partners see how they’re wired so they can appreciate each other’s differences instead of fighting them. A simple daily sync can cover energy levels, top three priorities for each person, and any decisions or blocks that need clearing so the day stays intentional. Weekly planning time lets you look back on commitments, learn from friction, and look ahead at upcoming meetings, travel, and priorities together. Entrepreneurs and EAs should regularly work on the partnership by reviewing what’s creating momentum and what’s slowing you down, then adjusting as a team. Monthly “stop, start, continue” conversations in both directions, plus daily SSS feedback (short, soon, specific), clear up unspoken expectations, improve teamwork and performance, and keep frustration from building up under the surface. Being open means being willing to receive honest feedback, not just give it, especially when it reveals your blind spots as an entrepreneurial leader. Terry’s example of his EA asking him to stop checking email showed how a small habit can unintentionally signal mistrust and create extra work for the team. Personality and profile tools make it easier to name differences so you can design meetings and roles that work for everyone. Many EAs want clarity on whether a meeting is for ideation or decisions so they can join at the right time and leave with concrete actions to execute. Staying in your comfort zone of Excellent activities can keep you overpaid for tasks you’ve outgrown and under-invested in the bigger future you say you want. The courage to fully delegate is often triggered when you commit to a bigger goal that simply cannot be reached if you keep doing everything yourself. Entrepreneurs who aren’t willing to grow, let go of control, or treat people respectfully are not ready for an EA and will burn through support quickly. If you treat an EA as a cost instead of an investment, you’ll miss the massive multiplication in time, energy, and opportunity they can create for you. The best EA relationships are built on mutual respect, shared values, and a genuine desire to protect each other’s Unique Ability and well-being. In the end, the entrepreneurs who get the most from their EA are the ones willing to be transparent, let go of control, and treat support as a strategic multiplier rather than a luxury. Resources: Superpowers Setting the Table by Danny Meyer Unreasonable Hospitality by Will Guidara Unique Ability® How To Sell Transformation Using This One Question The D.O.S. Conversation® by Dan Sullivan The Kolbe A™ Index Superpowered by Shannon Waller, Steven Neuner, and Ryan Cassin The Eisenhower Matrix The 4 C’s Formula by Dan Sullivan Frequency Assessment