Project Management

Helping Project Managers to Help Themselves

This blog is based on over 35 years of project management and leadership successes and failures. Get practical, concise nuggets on both hard and soft skills to help you deliver projects successfully with minimal friction.

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Shooting the Messenger

The 5 Tollgates of Selling Up-Part 5

The 5 Tollgates of Selling Up-Part 4

The 5 Tollgates of Selling Up-Part 3

The 5 Tollgates of Selling Up-Part 2

Shooting the Messenger

When I screw up, I have one way that I have found effective at helping me get through it and learn from it.

I write about it.

This is one of those royal jerk screw-up times.

Patty and I stayed at a hotel where we paid about $300/night. The room was clean and the location good, but the service and amenities were definitely substandard, certainly not something we’d expect from a $300/night room. The night before we checked out, we put together a number of issues and I sent it to the hotel’s customer service site, requesting a reduction in our room rate. The next morning, I talked with the hotel sales director about some of our issues. She was pleasant and empathic and said she would talk with the general manager.  A couple of hours later while driving we got a call from the sales director informing us that the hotel would not make any adjustment.

This is where the jerk part comes in.

I told - no yelled – that the sales director was making a mistake and that we were going to publish our issues with a poor rating on the travel website that we booked the reservation. After a couple more words I hung up. Patty was silent, which meant I was in the doghouse. I said to her, “Hilton would have given us better service.” That’s when she told me (rightly so) that I was rude to the sales director, that she was only the messenger, and that I should have never talked to her that way. The next 30 minutes in the car were pretty silent; I knew she was right and just needed a bit of time to reflect. We stopped at a Subway for lunch and while we split a turkey sub I told her she was right and how I shouldn’t have done what I did. After we arrived at our next hotel I emailed her an apology which she graciously responded to. Even with the apology, I’m pretty sure I won’t be getting a Christmas card from her.

I’d like to say that my primary motivation for writing this article was to give you something to chew on; actually, it’s more a reminder to me and if you get collateral benefit then all the better. Even after reflecting on my actions I still believe that me being disappointed with our stay at the hotel was justified. However, as I look back on my actions there are four things I did wrong:

  1. I shot the messenger – The sales director wasn’t the decision maker; she was only delivering a message from her boss. I neglected to acknowledge that she was only conveying a message, and that she wasn’t the decision maker.
  2. I talked to her in a tone she didn’t deserve – I wasn’t calm and measured in my demeanor; I was angry and I wanted her to know it. I could have gotten my point across just as effectively without turning into a Tasmanian devil.
  3. I let my ego get in the way of doing the right thing – When the sales director didn’t give me what I thought I deserved I took it personally and reacted as if her actions were personal. In reality, she was just doing her job.
  4. I damaged a relationship with a potential customer – Some would say that I’ll likely never see her again, so who cares? In my profession anyone wanting to learn more about leadership, project management, or disability inclusion is a potential customer. Any help I could have given her is likely an opportunity lost.

My point to not only you as my readers but as a reminder to me is as follows: be firm in your convictions but do it with respect. You don’t have to be a wet noodle and give in to others; just don’t be a horse’s hind during the process.

Posted on: October 16, 2021 04:37 PM | Permalink | Comments (2)

The 5 Tollgates of Selling Up-Part 5

“I’m in!” Lori, the department general manager said to Caleb. Caleb had just joined Lori’s department from a competitor where he had worked for two years after college. This was his first one-on-one meeting with Lori. Lori had a strong reputation as a people cultivator and looked for opportunities to grow her staff with in-the-moment learning opportunities. She was about to get that opportunity with Caleb.

“Great to hear. I can get going on the plan right away,” Caleb said.

“That’s great, now what do you need from me?”

Caleb stopped. “Um, I’m sorry?”

“What do you need from me?”

“Uh, nothing.”

“Nothing? Do you have the support you need from my management team?”

“Well, I was going to talk with them about it.”

Seeing the teachable moment opportunity, Lori decided to help Caleb think things through.

“Caleb, wouldn’t it be easier on you if the message came down from me that we needed to do this work and that they all should give you their full cooperation?”

“Actually, yes that would help.”

“And wouldn’t it help if I let finance know you were going to be coming to them with an ask for budget?”

“Yes, that would help too, Lori.”

“So you see where I’m heading, right?”

Caleb thought for a moment. “That I didn’t think about how you could help me?”

“Exactly. You did a great job of preparing with facts and data, convincing me there was a problem, and came in with a good solution that aligned with my priorities. You just didn’t think through what you needed me to do to help you. It’s my job to make sure you have what you need to do your job. If you don’t ask me to help you, you’re not letting me do my job. Does this make sense?”

“It does,” Caleb said.

“OK, now how about you put together your asks and we go through them tomorrow?”

“I will, thanks Lori.”

“Good work, Caleb. Can you send Radhika in on your way out?”

“Sure will. See you tomorrow.”

Tollgate 5: I get what you expect me to do

Getting agreement on a course of action is a huge win; to close the deal you need to be specific on what you expect the exec to do. This could be a simple, “Give me approval to proceed on the course of action.” It could also include garnering support from other executives, publicly expressing support of your course of action, or other steps. Whatever your asks are, make sure they’re specific and direct. Being wishy-washy means your exec may not do what you expect of him.

There are two considerations I’d like to highlight in this tollgate. First, make things easy on the exec by doing what you can to help with any asks. Want the exec to send an email to someone? Ghost-write the email. It not only makes things easier, but it ensures the exec says what you want. Second, be diligent on any follow-ups you are asked to do. You’d be sending a poor message if the exec asked you to do something and you weren’t timely in your response or even worse, didn’t do it at all. This could be a huge credibility hit and cause tollgate 1 problems next time you sell up.


We’ve gone through all five tollgates:

In wrapping up this series I’d like to leave you with a few helpful tips next time you have to sell up:

  • Make sure you structure your content to address each tollgate in sequence. If you haven’t passed tollgate 1, your likelihood of making it through the remaining tollgates is drastically reduced. Build your pitch around each tollgate in sequence.
  • Make your words count. More content isn’t better. Get your point across in as little content as possible.
  • Be manic about watching your exec’s reactions. If your exec is signaling understanding and you’re getting the desired result for a tollgate, move on to the next tollgate. I’ve had plenty of pitches where I’ve glossed over content because the exec was already on board with what I was presenting in a tollgate. The most important thing is to get what you want, not to showcase everything you’ve prepared.
  • Remember absolute vs. relative priorities. Just because an exec says, “Not now,” it doesn’t mean the exec is an idiot or that you’ve failed. Accept that timing might not always be on your side.
  • Structure content for time allotted and have a plan if that allotment changes. Plenty of times I thought I had an hour to pitch an idea only to have the exec tell me I only had 30 minutes. Anticipate what you’ll do in the event your time gets cut short.
Posted on: October 08, 2021 12:00 AM | Permalink | Comments (3)

The 5 Tollgates of Selling Up-Part 4

“Not now.”

Vic’s heart sank when he heard Tania, the VP of his division, utter the words. He thought he did everything right; made sure he had his facts right, clearly articulated the problem, and got Tania to acknowledge both the problem and his proposed solution. He thought it was a done deal. After the meeting, Vic went into Brenda’s office to vent. Brenda and Vic had been peer-mentoring each other ever since Vic joined the organization, so he felt safe confiding in her.

“I just don’t understand it!” Vic grumbled. “The problem is as clear as the nose on my face, and the solution is a no-brainer.”

“What did Tania say?” Brenda asked.

“Not now.”

Brenda leaned back in her chair. “Not now, eh?”

“Right, not now.”

“Let me ask you something,” Brenda said.


“See behind me? Those are Tania’s priorities for this year.”

“Yeah, I know, I’ve got that on my wall too,” Vic said.

“How does what you just pitched to Tania fit into her priorities?”

Vic looked through each item on the list. “Well, it really doesn’t, but this is still a huge problem that we need to fix!”

“And did she say it wasn’t a problem?”

“Well, no.”

“And was she supportive of your solution?”

“Yeah, but. . .”

“She said, “Not now,” which means there are more important priorities she wants to address. You know as well as I do that we’ve got finite resources to address problems; she’s being choosy about which ones to solve with the resources available. She’s just being a good leader by not randomizing her organization with a problem du jour. Does that make sense?”

Vic smiled. “Yeah, I see your point.”

“Good, now how about lunch, on you?” Brenda asked.

“Sure, meet you by the elevators in ten?”

“Yup, but if I’m paying we’re having sushi,” Vic smiled, knowing Brenda wasn’t a fan of raw fish.

“Cooked crab rolls for me, slimy stuff for you.”

Tollgate 4: I see how this aligns with my priorities

Making it this far through the tollgates means the exec acknowledges there’s a problem and understands your course of action. Now it’s about how the course of action you want to take aligns with other top-of-mind problems the exec is facing. Execs live in a world of competing priorities, all vying for mindshare, people, and money. Your job here is to ensure you understand the exec’s priorities and anticipate how your course of action aligns with the priorities. Many execs clearly document their priorities and make it easy for the organization to understand what they want done. Some, though, may have other items that aren’t on a published list. This could be due to recent events causing priorities to change or it could just be a lazy exec not taking the time to communicate those things that are top-of-mind for him or her. Whatever the scenario, your job is to understand what the exec’s priorities are and clearly articulate how your course of action aligns.

This is where the concept of absolute versus relative comes into play; something that many less-seasoned professionals have difficulty understanding. On an absolute basis, your course of action could be the right thing to do, but on a relative basis there could be higher competing priorities that need to be addressed before your course of action can be undertaken. This is where an answer like, “Great idea, just not now” can be given. This doesn’t mean your course of action is a bad idea, that you did something wrong, or that the exec is an idiot for not jumping on your course of action; it just means that there are bigger fish to fry. Embrace it as a fact of your professional life. 


You may have a great idea that addresses some business problem or seizes an opportunity. It’s not just a matter of convincing an exec of your solution; it’s also understanding how your idea aligns to the priorities the exec has top-of-mind. Take time to understand the priorities and be prepared to articulate how your solution addresses what your exec cares about.

We’ve gone through four tollgates thus far:

Next up is part 5 of The 5 Tollgates of Selling Up.

Posted on: October 01, 2021 12:00 AM | Permalink | Comments (3)

The 5 Tollgates of Selling Up-Part 3

"Gosh, this is a huge problem!” Renu said, leaning forward, elbows on the table, hands clasped in front of her.

Bert smiled, pleased with Renu’s reaction. Bert was a newly-promoted warehouse supervisor, having worked in the warehouse for two years fresh out of high school. He proved himself to be a hard worker with a lot of promise. Renu, the plant manager, saw Bert as a high-potential employee who had the passion and talent to ultimately take her job someday.

“I’ve been saying this was a problem for a long time,” Bert said.

“So what do you think we should do about it?” Renu asked.

Bert stopped for a minute, not expecting the question. “Well, I’m not sure.”

“You’re not sure?” Renu asked, her eyes locked with Bert’s.

“Um, no, not yet.”

“Not yet?”

Bert could feel the little droplets of perspiration forming on his forehead.

“Bert, you bring me a problem, but no proposal on what to do about it?”

“Well, I, uh, didn’t think we’d be talking about solutions here.”

Renu saw what was happening and decided to turn the meeting into a teachable moment.

“Bert, you and I have talked about your potential and you know how vested I am in your success. Anyone can identify problems; people who only identify problems are average at best. The ones who rise above are those who not just articulate a problem, but also follow it up with a proposed solution. Did you see how engaged I was when you articulated the problem to me?”

“Uh huh.”

“Right, I was bought into your problem. That was the time to articulate what should be done about it-- when you had my attention. When you come in without a solution to your problem it leaves me frustrated. I really want to know what you think and want to see your problem-solving skills in action. Does this make sense?”

Bert gave a slight smile, realizing that the meeting turned into a selling idea lesson. “It does.”

“Good, now how about we get together again in a couple of days and try this again.”

“Sounds good, I’ll get time on your calendar,” Bert said as he got up from his chair.

“Very good. Take care, Bert, and close the door on your way out.”

Tollgate 3: I understand what you want to do about it

After agreement on the problem, the next step is to articulate your course of action. This could be in the form of a target solution that addresses the problem or specific steps you think need to be taken to come up with a target solution. The important thing here is clarity. Whatever you propose, make sure it’s specific, quantifiable, realistic, and relevant. Specific means that you’ve drawn a clear line between the problem and the course of action; that it’s clear to the exec how the course of action addresses the problem. Quantifiable means that the course of action is measurable; that it would be clear whether or not the course of action was actually attained. Realistic means that the course of action can be realized given available time and resources; that the exec could secure what is needed to execute the course of action. Relevant means that the course of action is germane to the scope, values, and priorities of what the exec controls or has influence over; proposing something that is out scope of what the exec can influence will just get you a “I can’t do anything about this,” response.

By no means should you be like Bert and present a problem without a course of action. It labels you as someone who raises problems without recommendations on how to solve them. Anyone can raise problems; it’s the competent professionals who articulate what to do about them.

Again, positive engagement from the exec is crucial. Getting some questions and context is a good step to securing the exec’s buy-in. Things could get difficult if the exec disagrees with the course of action accompanied by your inflexibility to deviate from your proposal. Be very in tune to what the exec is communicating and look to incorporate some of his or her thinking into your course of action.


Execs can’t do all the thinking in an organization. They rely on competent, clear-headed thinkers to not just blurt out things that are wrong, but to articulate rational courses of action to make things better. Don’t leave an exec hanging with a well-defined problem and no proposed solutions.

We’ve gone through three tollgates thus far:

Next up is part 4 of The 5 Tollgates of Selling Up.

Posted on: September 24, 2021 04:00 AM | Permalink | Comments (3)

The 5 Tollgates of Selling Up-Part 2

“This is a big price tag,” Rhonda said as she looked through Tom’s proposal.

Tom didn’t expect the resistance he was getting from Rhonda, his organization’s vice president. Tom had just been promoted to manager of a small team and was in it to make a splash in the organization. He unveiled a bold proposal to implement new enterprise software that would replace an existing system that had been in place for several years.

“Yes, it’s a high price, but this is leading-edge technology that will help propel us into the future. Our current system uses old technology that will be obsolete. Now is the time to act.”

“But what we have is working and stable,” Rhonda said.

Tom’s frustration grew with Rhonda’s resistance. “Yes, today it’s working, but what about tomorrow?” Tom asked.

Rhonda looked at her watch. “Tom, we’re just about at time. Let me give you a bit of coaching.” Rhonda was big on cultivating her staff and used situations like this as teachable moments.

“Um, OK,” Tom said.

“I love your passion and creativity. Those attributes will serve you well as you progress in your career. Do you want to know where you missed the mark on this proposal?”


“You presented a solution without a problem.”

“Well, I . . .” Tom stammered as he flipped through his slides.

Rhonda stood up. “It’s not there, Tom. If you want to sell on a solution you’ve got to clearly articulate the problem you’re trying to solve. Give it some thought, OK?”

“I will. Thanks, Rhonda.”

“Take care,” Rhonda said as she left the room.

Selling up tollgate 2: I acknowledge the problem

Once you’ve made it through tollgate 1, I believe you’re credible, you now have to convince the exec that a problem exists. This is where objective facts and data take center stage. The key here is balance. If you come off like the black and white opening scene in an infomercial with a person feigning utter disgust while trying to peel a potato, then you’re going to be viewed as jaded and will undercut your own credibility.

Also key to explaining the problem is articulating the consequences of not addressing the problem. When an exec not only understand what the problem is but also has a clear picture of the tangible consequences of not addressing it, you’ve accomplished both explaining what the problem is but why it’s important to address.

So what about if what you’re trying to sell isn’t a problem that needs fixing but an opportunity that needs to be seized upon? The approach is no different. Support the opportunity with objective facts and data and explain the consequence in terms of what happens if the opportunity isn’t pursued.

As with tollgate 1, look for positive engagement from the exec. Confrontation on the problem statement could mean you haven’t convinced the exec there’s a problem, and silence on the exec’s part could be a sign of disinterest.


Execs live in a world of problems to solve, and constantly have to decide which problems to pursue and which to leave on the back burner. If you want your exec to take action, you have to convince him or her that there’s not only a problem, but it’s one worth pursuing. Next time you propose a solution take the deliberate step to clearly articulate the problem you’re trying to solve.

We’ve gone through two tollgates thus far:

Next up is part 3 of The 5 Tollgates of Selling Up.

Posted on: September 15, 2021 06:30 PM | Permalink | Comments (3)

"If you can't be a good example, then you'll just have to be a horrible warning."

- Catherine Aird