How to be a Badass Delegator

Squared Away’s delegation guide will help you offload work from every aspect of your life.

Michelle Penczak
May 28, 2020 · 6 min read

At Squared Away we believe in supporting the whole individual and/or team. Both personally and professionally. Sometimes there are priority tasks in both areas and you can’t focus on one without worrying about the other. That’s where Squared Away comes in. We are here to support ALL of your priorities and assist you reaching (and exceeding) your desired timelines.

Why Delegation Works

➔ Administrative tasks can typically be done with universal competence.

➔ Creating invoices, scheduling, booking travel, or conducting research are all things that have little to no variation if someone else does it.

➔ When you find yourself spending hours on it, realize that you can and should be spending your time elsewhere.

➔ Allows you to focus your expertise on what really matters.

What Your Assistant Can Do

  1. Identify high value — low risk tasks
  2. Decide to drop, delegate, or re-design tasks
  3. Off-load tasks
  4. Allocate and free-up time
  5. Commit to your plan

How to Begin Your Delegation Journey

Accept The Fear Self-sabotaging statements like, “I can do it better myself,” or “I can’t fail,” or “I don’t want to depend on anyone else,” or “I can’t trust them,” will hinder your ability to delegate. Acceptance will empower you, give you peace of mind, allow you to be free to see the bigger picture, and prepare you to be a master delegator.

It’s not whether or not you can complete the task on your own, but to ask yourself what’s the return on investment by doing so? Low-return tasks like scheduling, booking travel, or research have less of an impact on your profession. Focus on high-return tasks: strategy, new hires, partnerships, or organizational structure.

You’ve gotten to this level by trusting yourself and others trusting you. Trust that your assistant will get the low-return tasks done for you just as well as you would have.

Start with some of these basic tasks that are high-time consumption low-return.

Calendar Scheduling- have an assistant manage your calendar. Start by cc’ing them on any meeting requests. They will find the time that works best for all participants and add it to your calendar. Anything that goes in your calendar should go through your assistant. Your assistant is your gatekeeper, simply cc’ing them on emails will entrust they are handled.

Spend your time strategizing for your board presentation, not researching next year’s trends.

Your assistant will handle the research and give you complete thoughts in easy-to-read bullets with sources.

Your assistant will also handle any travel or hotel bookings. She will take care of everything, add it to your calendar, and ensure you have a seamless experience.

When you are going to a new city and have to take a vegan client out to lunch, your assistant can find the best place a short walk from your client’s office.

Your office is growing, and you need to find a new space, near public transportation, and the freeway. This is something your assistant can research for you, and also something they can coordinate tours for so you can optimize your time by arranging multiple visits in a single trip.

It never hurts to get a second set of eyes on a document. Delegate proofreading to your assistant to double-check any grammatical or syntax errors.

Plan Ahead Author of “Never Eat Alone,” Keith Ferrazzi shares how he built his career.

Researching anyone with whom he had a meeting before they met so that during the meeting, he’d be able to engage in meaningful conversations. Similarly, people who successfully delegate plan their tasks out and identify the items they can delegate. They think big-picture about what they need to accomplish.

People delegate to strive for efficiency in completing tasks. Keeping efficiency top of mind prevents them from falling back into an old, inefficient mindset.

Instead, they maximize the effectiveness of their every endeavor and promote efficiency around them. They’re also focused on the end goal (task completion) and comprehend there will be multiple ways to reach it, taking the most efficient path to get to it.

Delegation isn’t merely the ability to unload work onto someone else. It’s an opportunity to maximize the productivity of an entire group or system. It’s the ability to spread crucial tasks among a set of hands, picking and choosing the most appropriate places.

Successful delegators act as quarterbacks, throwing a task to the delegatee with a touchdown in mind. When a lousy pass is thrown, it ends up causing strife for the entire team.

Every task has a start and finish. As a delegator, you can offload action, but responsibility remains in your camp. This looks like providing feedback, checking for errors, or sending a simple “thank you.”

Not closing the loop leads to other issues where the delegatee doesn’t know if it’s time to move onto the next task.

Our days regularly change; we wake up planning to meet a coworker for breakfast only to find that our car battery has died — time to move things around.

Delegating is no different! An assignment you planned to do may become superseded by an urgent task. Try to circumvent this by making a to-do list every morning and share it with your delegatee.

Once reviewing the list, you can figure out which tasks you should handle while your assistant takes the rest. If something unexpected pops up, re-visit your priorities and rearrange them as needed.

Successful delegators continuously plan for the future.

When it comes to working, they remain consciously aware of what they accomplished, what they’re working on, and what they’re doing next.

That means they’re able to focus 100% of their energy on one thing, finish it, and move onto the next with little disruption. Being reactive poisons productivity and hinders successful delegation. It keeps you in an unnecessary, constant state of worry where you’re always playing catch-up.

Setting immediate, short-term, and long-term goals keeps you in a proactive mindset. Along the way, you will need to delegate tasks to an assistant and once you’ve laid the foundation for successful delegation, you’ll see how easy it supercharges your productivity.

The Do’s and Don’ts of Delegation

  • Identify low-value tasks
  • Decide to drop or delegate
  • Offload those tasks
  • Allocate free time to other areas
  • COMMIT to your plan
  • Self-sabotage (“I can do this better myself” or “I don’t want to depend on anyone else”)
  • Accept the fear (You’re in great hands with us –guaranteed)
  • Consider the return (low-value tasks aren’t going to risk your job and will save you time & the energy in the long run)
  • TRUST that your assistant will get the job done as well as you

Delegation Ideas

  • Scheduling: Calendaring, service arrangements, appointments, etc.
  • Travel Planning: Airlines, hotels, dinner reservations, vehicles, etc.
  • Finance: Bookkeeping, payroll, and expense reports.
  • Optimization of Expenses, Perks, and Credit: Best programs/cards, upgrades, getting to the front of the line, etc. and credit optimization.
  • Optimization of Sales Team: Tracking time, meetings and task management
  • Marketing: Social Media (Instagram, Twitter, etc.), mailing services
  • Setting up and managing video or podcasts (Chase Jarvis Live, Ask, etc.)
  • Research: Content (blogs, social networking, podcasts), products, or competitors
  • Content Writing/Editing/Proofreading: Speeches, blogs, website content, WordPress, etc.
  • Organization: Location transition (home or business) and get yourself organized
  • Home services: Cleaning, housework, meal cooking/delivery
  • Purchasing: Corporate gifts, professional and personal shopping
  • Welcoming services: Greeting newcomers, ordering samples and signs, community information from or to local businesses, etc.
  • Party/Event planning: Company parties, personal events, children’s parties, and other events — negotiating pricing, catering/alcohol, finding venues, entertainment extras (party favors, special guests, music, etc.)
  • Dinners: Thought-leadership dinners (similar to Ask dinners) or dinners/events for special customers (including handwritten notes for guests, client-oriented preferential treatment, etc.)
  • Company/Team Events: Monthly events/mixers
  • Team Offsites: Teambuilding or immersions at resorts, conferences, etc.
  • And so much more. If you can dream it, we can do it!

Squared Away is comprised of military spouses who are your trusted assistants. We help CEOs, VCs, executives, and startup teams get their time back. US-based. #SquaredAwayLife #ChiefExecutiveAssistant

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