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Dan Kelly: “Delegate goals and outcomes and not pathways”

Delegate goals and outcomes and not pathways. State your objectives precisely so that the person understands what you require of them. Focus less on methodology and more on the end goal, ensuring that the person understands how they will achieve that. Use exact parameters when explaining what needs to be done. For example, if you […]

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Delegate goals and outcomes and not pathways. State your objectives precisely so that the person understands what you require of them. Focus less on methodology and more on the end goal, ensuring that the person understands how they will achieve that. Use exact parameters when explaining what needs to be done. For example, if you delegate to someone to compile a presentation, don’t explain every nitty-gritty detail of slides layout, images, and fonts. Just outline the end results you would like to achieve with this presentation.


As part of my series about the “How To Delegate Effectively and Be Completely Satisfied With the Results”, I had the pleasure of interviewing Dan Kelly.

Dan is a Founder and Senior Partner of The Negotiator Guru, #15 on INC 5000-Midwest, and the 2nd fastest-growing private company in Minneapolis. Top corporations trust The Negotiator Guru with sourcing, negotiating, and managing highly complex IT contracts. Dan is a host of the State of the CIO podcast and a global thought leader in advanced negotiation and IT strategic sourcing.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Negotiations are my passion. For me, they are a craft that, once mastered, makes everything possible and opens every door.

Many people think that skilled negotiators are liers. This is a misconception. The best negotiators are honest; they build trust and are incredibly empathetic. Since I was very young, I felt a great pleasure negotiating win-win solutions with my parents, friends, and even my school teachers. I just loved seeing how fair and honest negotiations can create positive outcomes for everyone involved.

My passion for negotiations led me to the FBI, where I started my career and was in charge of Strategic Supplier Relationships. However, four years later, I discovered that being a government employee wasn’t for me. I wanted to be paid for performance and have unlimited growth opportunities.

After leaving the FBI, I tried myself in multiple leadership roles in companies like Cargill, Syngenta, and MTS Systems. But I always felt that I wanted to do something more. I knew that I could run my own show and have a much more significant impact on a global scale. So I founded The Negotiator Guru in 2015 to support the businesses’ real needs and solve real-life problems for my clients on every continent. Now TNG is #15 on INC 5000 Midwest and 2nd fastest-growing private company in MN.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

There are no easy times when running a business. It’s always challenging times. What are “hard times”? It is when something doesn’t go as planned. And if it doesn’t, it means that YOU failed to plan, make enough money, or have a backup strategy if the initial plan doesn’t work.

My most challenging times were when I was starting. I did not know anything about recruitment or HR. I wanted to hire a great team quickly and get running. So I decided to do it myself without any outside help and moved too fast without adopting my processes. So once I had my first revenue spike, I decided to double our headcount at the time. Once I realized that my overheads were higher than my income, I had to re-structure, re-align our strategy, and make sure that we get enough business to continue running the company. So we shifted our focus entirely to lead generation to grow our customer base. I am still amazed how we overcame this challenge as a team, and instead of cost-cutting, we make through these hard times by pushing our revenues up.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

One of the funniest mistakes I made was double-booking my calendar with meetings several times. It caused me a lot of embarrassment and fire-fighting. I learned from it that I should always use one calendar app across all the devices and throw the traditional paper agenda away!

What do you think makes your company stand out? Can you share a story?

We offer something very unique to our clients. Now that digital transformation became necessary, IT expenses are going up. So many software developers are using the spike in demand to grow their profits. We negotiate on behalf of our clients and reduce their IT Software expenses by up to 50%. In the end, everyone wins: our clients save, and software developers gain long-term customers instead of losing them to competitors. I guess there are not many businesses that can say that their goal is to make everyone win.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Identify and eliminate stress triggers by noting them down. Have a notebook next to you and write down when you feel stressed and what you are doing at a specific moment. Review your notes every few days and ask yourself if you could eliminate these tasks or change the process by delegating them to others. This technique will improve your mental health and eliminate stress.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I am grateful to my mom, who served as my inspiration throughout my life. She was a hard worker and always succeeded in achieving her goals and make us proud.

Ok thank you for all that. Now let’s shift to the main focus of this interview. Delegating effectively is a challenge for many leaders. Let’s put first things first. Can you help articulate to our readers a few reasons why delegating is such an important skill for a leader or a business owner to develop?

You must delegate to focus on what’s essential, continue running your business, and continue managing your finances effectively. If you do everything yourself — at some point, you have no more leads, no more clients, and no more money. Another benefit of delegating is that your people feel empowered and trusted; they learn new skills and stay motivated.

My first experience delegating responsibilities was life-changing. My company was growing when I finally had to hire my first executive. One day he came into my office at 8 PM and saw me working on my laptop. He asked, “Dan, what are you doing?” I told him I was working on proposals.

He said, “With all due respect, you should be delegating such stuff so that you can run the company.” His advice was spot on. I was obsessed over every tiny task that I could delegate. From that day, I worked hard to learn how to trust my team and focus on things that would drive my business forward.

Can you help articulate a few of the reasons why delegating is such a challenge for so many people?

People are naturally afraid of change and doing things a new way. Delegating means accepting that you let go of control and that there are different ways to solve a problem or complete a task. Delegating requires a change in perspective. Stop being afraid of failure and thinking that no one else can do the job better than you.

In your opinion, what pivots need to be made, either in perspective or in work habits, to help alleviate some of the challenges you mentioned?

Before overcoming the fear of delegation, ask yourself, what are you precisely afraid of? Are you worried about losing control? Missing project deadline? Letting down your customers? Once you know your fears, think of how you can minimize them. For example, if you are afraid that the deadline will be missed, set up a follow-up system. Use project management tools and make a running task list. Hold weekly or bi-weekly meetings to review the progress. Use reminders to keep track of the deadlines.

To ensure that the job is done well, provide your team with necessary trainings and resources (for example, screen recordings of a particular process), be available to answer questions, and welcome new ideas.

Can you please share your “Five Things You Need To Know To Delegate Effectively and Be Completely Satisfied With the Results?” Please share a story or an example for each.

1) Do not delegate to give yourself less responsibility. Align your responsibilities properly with where to best spend your time. Understand the tasks and responsibilities you are delegating to be able to step in when things go wrong. For example, when you are delegating to your sales rep to negotiate a contract with the client, make sure that you are prepared to step in if things go wrong.

2) Give people space to breathe and accept when things are not done the way you like them. Delegation is an act of trust and decentralization. The person you delegate a task needs to have the freedom to improvise and make mistakes.

3) Delegate goals and outcomes and not pathways. State your objectives precisely so that the person understands what you require of them. Focus less on methodology and more on the end goal, ensuring that the person understands how they will achieve that. Use exact parameters when explaining what needs to be done. For example, if you delegate to someone to compile a presentation, don’t explain every nitty-gritty detail of slides layout, images, and fonts. Just outline the end results you would like to achieve with this presentation.

4) Set firm dates for “report and completion.” If you delegate a task, set a meeting or a call date right away to report on the progress. Continue monitoring the progress along the way to ensure that the person stays on the right path. Make it clear that you are ready to help at any point. Monitor, but don’t micromanage.

5) Conduct an assessment once the project is done. Ask your team to evaluate your performance as a leader and their own. Ask questions like, “What would you have done differently?” “What went well? Why?” “How could I have better helped you throughout this process?”

One of the obstacles to proper delegating is the oft quoted cliche “If you want something done right do it yourself.” Is this saying true? Is it false? Is there a way to reconcile it with the importance of delegating?

This statement is false. True leaders shine through the work that is done by their people. The assumption that if you want something done, do it yourself is arrogant because it shows that you believe that your way is the only right way. Teaching others and helping them grow has tremendous social value. If you are really good at what you do, share your skills and knowledge with others to add value to society, and enhance your team.

Thank you for all of that. We are nearly done. You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I would start a movement: “Effective Negotiations Can Change Lives.” I would create educational centers across the globe to educate people and teach them the art of negotiation. It can open endless job opportunities and foster entrepreneurship and innovation in the poorest corners of our Plant. Once people become empathetic, honest, and fair negotiators, they can change the world — one win-win negotiation at a time.

How can our readers further follow you online?

My LinkedIn: https://www.linkedin.com/in/dankelly1/

This was very inspiring. Thank you so much for the time you spent with this!

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