Helping Project Managers to Help Themselves

Recently I had an interesting interaction on LinkedIn. A fellow from a financial services company asked to connect with me, which I accepted. He immediately sent me a message asking to meet for coffee to conduct a personal financial review, and told me his other customers were VERY (yes he “e-yelled” VERY) satisfied with the work he did. Aside from the fact that I’m satisfied with my existing financial advisor, I have a bit of a problem with someone on LinkedIn pitching me right after connecting. I replied with a simple “No Thanks.”

A few days later he responded back thanking me and asking why I declined. I had to decide whether to just ignore his question or respond. I looked at his profile and decided that he really wanted to know and that I could help him with his connect à pitch technique. I told him that I thought his trying to sell me right after connecting was disingenuous; that he didn’t take any time to learn about me and didn’t try to develop any rapport points. He then responded with “When did I try to sell you?” I told him that asking to do a personal financial review and telling me his other customers were VERY satisfied felt like he was pitching me. He then responded with “When did I ask to review your personal finances?” At this point I was curious as to where this was going, so I did a copy/paste from his original message that asked to do a personal financial review. This is where it got really interesting. He responded with the following:

“I never asked you to share your personal financial information online. It was a simple yes or no question. Most nice people on LinkedIn are happy to meet up with me for a chat over coffee. At this point I’ll pass on my offer to meet with you. Best of luck to you in the future.”

I read his message, partly amused, partly shocked. I thought it interesting how he inserted the word “online” in his response (which was never mentioned before), how it was a simple yes or no question (which I answered initially with a simple "no"), how nice people are happy to meet up with him (I guess I’m on his naughty list now), and how he’ll pass on his offer to meet up (kind of felt like “You can’t break up with me, I’m breaking up with you first”). He did put a “Best of luck to you in the future” tag on the end to pretend to be professional, but it wasn’t enough to prevent me from blocking him.

I mused over this interaction and decided to call one of colleagues to get her take on what happened. I told her the story and after saying, “Thanks for making my day,” she confirmed that this was a textbook example of a disingenuous sales interaction. While I was pleased that I didn’t totally misread things, the consultant in me hoped the fellow would have used the feedback as a teachable moment. He asked for feedback, didn’t like it, then told me I wasn’t nice. He did give me one gift; great content for an article.

My one takeaway for you is this: as a leader if you’re going to ask for feedback, be prepared to get feedback that you may not agree with. That doesn’t mean you have to act on the feedback; it does mean, though, that you should try to understand it and acknowledge it with grace. I made it clear to the fellow that my job was to tell him what I thought, his was to decide what to do with it. He could have just said “Thank you, Lonnie,” and went on his way. He took the additional step to not only ignore the feedback but try to prove me wrong and subsequently insult me. He never considered the position he was putting me in. I could have simply ignored his request for feedback, but I thought he really wanted to know why I didn’t want to meet up. Turns out he didn’t give a rat’s tail about what I thought. It was all about him. You can add the words “lack of grace and maturity” to disingenuous when I think of this person. I may forget his name, but I will always remember the company he works for. That company will never get my business.

Asking for feedback doesn’t mean you have to act on it. By all means, if you don’t understand feedback, ask clarifying questions to help you decide what to do with it. But don’t insult the person you asked; they don’t deserve it.

In Part 1: Ten Differences Between a Secure and an Insecure Leader,  I contrasted ten key attributes that distinguish a secure leader from one who is insecure in his or her abilities.  Part 2 is dedicated to giving you eight nuggets to help you succeed under an insecure leader. 

For years I was an insecure leader.  My greatest fear in leading others was that I would be "found out" and that everyone would see me not as a strong, competent leader but as a bumbling fool.  Through the years I've learned that the quest for infallibility is impossible to reach and that making mistakes is part of the growth process.  I'm less insecure today because I am more comfortable saying "I don't know" without everyone in the room thinking I'm an incompetent twit.  Having said that, I am secure in knowing I will continue to screw up until my last breath.

For an insecure leader, it all comes down to trust.  Insecure leaders are by default distrustful of others and will only let those into their inner circle after trust has been earned.  You could be the best performer in the leader's organization but if he or she doesn't trust you then you're always going to be operating on the fringes with the leader and will likely have a stressful relationship.  Unfortunate, yes; but that's the fact Jack. You need to accept and embrace it.

So okay, you've accepted and embraced the fact you work with an insecure leader.  What next?  Here are eight specific things to consider in better securing a good working relationship with the leader:

Respect the leader's position - Regardless how smart or competent you feel your leader is, the first step to a healthy relationship with an insecure leader is respecting his or her position as leader.  To an insecure leader, disrespect for the position is no different than disrespect for the leader.

Don't overdraw in the feedback bank account - Insecure leaders need to hear that they are doing some things right.  When presenting feedback to the leader, start things off with something positive before raising constructive feedback.  The spoonful of sugar will truly help the medicine go down better for the leader.

Don't dump problems - If you have a difficult issue you need help with don't dump it on the leader's doorstep.  Clearly articulate the issue and present some alternatives to how you and the leader can resolve the problem together.  Dumping the problem can put insecure leaders on edge because they may now feel as if they are being tested.

Criticize in private - Publicly criticizing or embarrassing an insecure leader puts the leader in a "fight or flight" situation and can severely damage your relationship with the leader.  Save the negative feedback for a private session.

Don't suck up - A savvy leader will see sucking up as insincere.  In addition, other team members will resent you if you are viewed as a brown-noser in it for personal gain. 

Allow the leader to teach - Being insecure doesn't necessarily mean the leader is incompetent.  Find something you can learn from the leader and become a student of the leader's viewpoint.  Being less than open to learning something from the leader may suggest a problem with your attitude versus purely a problem with the leader.

Understand the leader's communication style - Some leaders truly are "open door" while others prefer scheduled appointments.  Some prefer verbal discussion while others like written emails.  Understand how the leader likes to communicate and stick to his or her style.  Also beware of the leader who says the politically-correct "my door is always open" but seems annoyed if someone barges in.  Keep your ear to the railroad track and understand how the leader truly likes to communicate. 

Don't compromise your principles and values - learning how to work with an insecure leader doesn't mean blindly following whatever the leader asks you to do.  If an insecure leader asks you to do something against your principles be very clear in articulating your objection and why you are objecting. 

My one nugget to you is this: recognize you work for an insecure leader, embrace it, and decide you're going to make the best of the situation.  It will not only yield a better working relationship with your leader, it will also reduce your stress level.

Some time back I was talking with a fellow project manager about a difficult issue he was having with his new boss.  The thumbnail summary of the discussion was that the project manager was feeling overly scrutinized and micro-managed.  Now I knew the project manager to be a capable professional who could confidently handle the work assigned to him.  Yet his boss insisted on managing every detailed aspect of his work.  More so, his boss was very critical of the work being done even though it was performed to professionally acceptable standard.  The situation became unbearable for the project manager; he ultimately left the organization. 

As I thought about this situation, I noticed an interesting parallel to other leadership situations I have seen and been part of.  Both the project manager and his boss had similar backgrounds and similar years of experience.  Although the boss had been a manager for years, he tended to surround himself with younger, more inexperienced managers. Having a more senior and experienced project manager reporting to him was clearly something that took him out of his comfort zone.  Rather than embracing the experience, the boss felt threatened by the project manager and worked to "keep him in his place".  

As I added things up in my mind about the situation one thing came clear; the boss' own insecurity was a key problem driver and was hampering the group's potential. 

This situation caused me to start thinking more about the attributes of secure and insecure leaders.  After noodling through I settled on ten key differences between an insecure and a secure leader. Give these a look and see if any resonate with you:

1. Insecure leaders selectively divulge and withhold information.  Secure leaders freely share information.
2. Insecure leaders teach employees what they need to know.  Secure  leaders nurture employees to help them figure out what they need to know. 
3. Insecure leaders discourage risk taking.  Secure leaders encourage calculated risk taking.
4. Insecure leaders give instructions and expect them to be followed.  Secure leaders give guidance and expect results.
5. Insecure leaders demand respect.  Secure leaders earn respect.
6. Insecure leaders may acknowledge great performance but ensure they also get credit.  Secure leaders spotlight great performance and don't worry about getting credit.
7. Insecure leaders hire and promote others who think like they do.  Secure leaders hire and promote others who think differently than they do.
8. Insecure leaders deflect failure.  Secure leaders accept responsibility for failure.
9. Insecure leaders promote those they can control.  Secure leaders promote those they don't have to control.
10. Insecure leaders grow good doers.  Secure leaders grow great leaders.

The one nugget here is this: honestly think through whether or not you are an insecure leader or a secure leader.  If you fall on the insecure end of the spectrum, do some deep soul-searching as to what is causing you to feel insecure about your leadership abilities.  Find a trusted mentor or colleague to help you dig into things and to shore up the areas which you need to address.  Recognition and acknowledgement of your improvement areas is the most important step to growth.  Don't kid yourself into thinking you're something that you're not. 

Want to know how to succeed under an insecure leader? See part 2: How to Succeed Under and Insecure Leader.

  So let's get right into this....

Ever known a manager who held great respect of his or her team but was not respected by his or her management?  Or maybe you've had a manager that just couldn't get things done effectively because he or she just didn't know how to "work the system"?  Or even still, are you are a manager who is continually frustrated because you can't get your manager to do what you need him or her to do?  If any of these sound familiar to you, welcome to the world of ineffective upward management. 

Upward management is one of those skills that some do very well, many never seem to master, and virtually all learn only through on-the-job lessons-learned.  When done well, both the manager and employee work as a team to ensure each other is informed, address problems before they spin out of control, and be more effective at managing.  When done poorly, both manager and employee are not only ineffective at getting the job done but are chronically frustrated due to missteps and surprises. 

Through the years I've come to categorize most poor upward managers into four personality types:

• The Brown-Noser - This is the employee who treats his boss as some kind of rock star and constantly searches for what his boss wants to hear.  Rather than upwardly managing, the brown-noser upwardly affirms whatever it is the boss is thinking.
   
• The Rebellious Teenager - This is the employee who consciously conceals information from her boss because she wants to demonstrate that she can get things done without help from her boss.  Rather than upwardly managing, the rebellious teenager keeps her manager in the dark by withholding information.
   
• The Cowardly Lion - This is the employee who simply is afraid to share information with his boss because he fears his boss' reactions.  Rather than upwardly managing, the cowardly lion avoids sharing information unless completely painted into a corner.
   
• The Erupting Volcano - This is the employee who subscribes to the "more is better" school of information management and will tell her manager every gory detail of every single event every single day.  Rather than upwardly managing, the erupting volcano spews data like hot lava and forces her manager to pick out the important facts.

So how do you avoid missteps in managing upward?  Give this baker's dozen a look and see if one or two of these nuggets can help you be a better upward manager:

• #1 - Understand your boss - Think about how your boss likes to communicate; does she prefer written emails or verbal discussion?  Does she like structured one-on-one meetings or informal chats?  Get a clear understanding of how your boss likes to engage and adapt your style to her style. 
   
• #2 - Stick to objective facts - When presenting information avoid emotionally-biased assessments.  Sure, you may have put your heart and soul into a project but if the project no longer makes business sense to do then it's your responsibility to put personal feelings aside and do the right business thing.
   
• #3 - Don't dump problems on his or her doorstep that you should be solving yourself - Yes, your manager has greater responsibility than you, probably gets paid more than you, and most likely has more organizational influence than you.  That doesn't mean you get to delegate things you should be solving yourself.  Handle the problems that you're paid to handle and enlist your boss for the stuff that requires his influence in the organization. 
   
• #4 - Be specific about what you need - Whether it be money, resources, or some other form of assistance, be very specific about what you need, why you need it, and what will happen if you don't get what you need.  Credible objectivity is crucial here:  if it looks as if you are "stacking the deck" by exaggerating consequences or embellishing benefits you're likely to not get what you need.  Also, subsequent asks are going to be viewed with greater skepticism. 
   
• #5 - Don't ever give reason for your boss to question your credibility - Simply put, if you get caught stretching the truth on even the smallest of facts, you've now given your boss reason to question not only the little things but also the big things.  You've got to stay pure with your boss and protect your integrity by never allowing your credibility to be put to question.
   
• #6 - Don't manage upward at the expense of managing downward - I've known one too many managers who did a great job of keeping his boss happy but had a team that wanted to string him up by his thumbs.  Look, at some point in time those that manage up at the expense of managing down will get found out and will have to pay the piper.  Don't play Russian roulette with your career by keeping your boss comfy while ticking off your team. 
   
• #7 - Respect your boss' time - Got a meeting with your boss?  Show up on time, come prepared to discuss whatever topics need discussing, and end the meeting on time.  Your boss is busy and her time should be utilized as effectively as possible.  Don't let your boss see your meetings with her as a waste of time.
   
• #8 - Diligently follow through on commitments - So your boss asks you to complete an assignment by tomorrow.  You agree to meet the commitment.  The deadline passes and you haven't met the commitment and all you can offer up is some lame excuse.  Sheesh.  Even if you think an assignment given to you is the dumbest assignment on earth, if you've made a commitment to do it then meet the commitment.  Not following through shows a lack of respect for your boss and breeds distrust. 
   
• #9 - Present options - In decision making managers like to see alternatives and the consequences associated with each alternative.  Some of the best decision making meetings I've been in with my bosses have been where we had meaningful dialogue around two or three viable options to resolving a tough problem.  My job in the process was to frame up the options, provide facts to support each option, and provide a recommendation.  Sometimes the recommendation was taken, sometimes not; the most important thing was that a good decision was made because there was good informed discussion.
   
• #10 - Make your boss look good - Let's say that your boss is due to make a presentation to his boss and is relying upon you to provide some critical information.  You give your boss the information he needs and he presents it to his boss.  He then gets fricasseed because the information is wrong.  Guess whose office he stops at first on his way back from getting barbecued?  Simply put, don't put your boss in a situation where he looks bad in front of his management; you've not only hurt your credibility, you've hurt his credibility.  
   
• #11 - Don't suck up - Telling your boss what she wants to hear can label you as a spineless know-nothing who doesn't have the intestinal fortitude to manage effectively on your own.   You'll not only quickly lose the respect of your team, your boss will ultimately see through you and not respect your leadership abilities.  Sure, you may get the occasional self-absorbed manager that craves shameless idolatry; but by and large bosses view sucking up as incompetence.

• #12 - No surprises - Ever tell your boss that your project is on schedule and on budget then at the last minute spring a huge schedule or budget slip on her?  Particularly early in my career I've had this happen more than once.  For it to happen more than once is shameful to say the least.  Bosses don't like surprises where they are forced to accept a problem without having the option to try to fix it before it got out of control.  When you see problems make sure you northwind your boss; just make sure you're working diligently to resolve the problem and not just to cover your @$$.  

• #13 - Admit mistakes...quickly - Look, screw-ups happen.  Heaven knows that I've got more screw-ups to my name than many managers will ever see.  The important thing is to own up to your mistakes quickly and outline what you are going to do to rectify the mistake.  Being the last one to recognize you've made a mistake just diminishes your credibility, so own up to those gaffes and get to work fixing them.  

A sad tale of a how a sponsor/PM relationship killed a project...

Exec identifies a need for a project and nominates self as sponsor.  PM gets assigned to project and assembles project team.  Sponsor is vague about problem to be solved other than "we need a new system".  PM can't communicate problem to be solved to the team because he doesn't understand what the problem is.  Sponsor continues to ask for more and more things to be included in project, PM doesn't have courage to say no.  PM treats sponsor as "that person in the corner office" and doesn't know how to ask for help, so he escalates everything.  Sponsor has to make some tough decisions but is unwilling to do so because of the political fallout.  PM provides bad information about decision alternatives so sponsor ignores him.  Due to changing priorities project no longer makes sense to do, but PM lobbies to keep the project going.  Sponsor loses interest because there are bigger fish to fry.  PM and team are disillusioned because sponsor doesn't care.  Project dies a slow death.  R.I.P.

While this is a fictional story, you can undoubtedly relate to most of these things happening on one project or another in your career.  The sponsor/PM partnership on a project is one of those "soft skill" factors that gets frequently overlooked when assessing a PM's skills but is a key determinant in the success or failure of a project.  Under a healthy partnership, the sponsor and PM work as a singular unit to ensure the project gets what it needs to be as successful as possible using only as many resources as absolutely necessary to secure success.  Under a less than healthy relationship the project will undoubtedly cost more in time and money assuming it even gets completed at all. 

Throughout my career I've been both a sponsor and a PM and have first-hand experience in how this relationship needs to work from both sides of the desk. Through my experience, I've locked down on ten truths which I feel are crucial to securing a healthy sponsor/PM partnership.  See if these resonate with you:

Truth #1: Great sponsors clearly articulate a root-cause problem to be solved. Great PM’s make sure the team knows (and remembers) what problem is being solved.   No surprise that great projects start with a great problem statement.  Where things go awry is when there's fuzziness about the problem statement between the sponsor and PM and when they aren't completely unified on the problem being addressed.  The sponsor needs to be clear about the problem, the PM needs to keep it at forefront and never allow the team to drift from solving the problem.

Truth #2: Great sponsors ensure the solution solves the root cause problem. Great PM’s don’t allow solutions to lose focus. It's so easy for a project team to get all lathered up in the coolness of a solution and the incremental value which can be had by just taking on a bit more scope here and there.  I love when project teams can kill two birds with one stone, but at the same time the sponsor and PM need to be very disciplined about keeping the project team focused on solving the root cause problem and not allowing scope to explode due to emotional frenzying. 

Truth #3: Great sponsors enforce a “good enough” mindset. Great PM’s don’t use “good enough” as an excuse to cut scope. Using a "good enough" mindset means being very conscious of not gold-plating a solution and putting incremental work into a feature that doesn't yield incremental benefit.  PM's, project teams, and sponsors alike fall subject to gold-plating to increase coolness or solve out-of-scope problems.  The sponsor needs to continually remind the team to not gold-plate and to do what's required to solve the problem.  At the same time, the PM can't use good enough as license to trim scope to solve a budget or schedule problem.  Certainly budget and schedule problems will happen, but the PM can't hide behind good enough and unilaterally trim scope based on his or her convenient definition of what good enough means.

Truth #4: Great sponsors ensure the project has the right resources to get the work done. Great PM’s articulate clear resource requests and “right size” the ask to the need.  No news flash here; projects need people and money to get things done.  Where things go awry is when project needs are poorly articulated, lack credibility, or are flat-out ignored.  This is one of the most important areas of an effective sponsor/PM partnership.  The PM needs to be crystal clear about what resources are needed to complete the project, thoughtful about alternatives to fulfilling the need, and objective about the consequences of not filling the need.  The sponsor needs to be convinced of the resource need, then needs to either support the PM to secure the resources or understand and accept the consequence of not securing the resources.  This truth is a massive failure point in projects with both the sponsor and PM being culpable.

Truth #5: Great sponsors hold the PM and team accountable for results. Great PM’s embrace the accountability and enforce it with the team.  Any leader worth his or her salt understands the concept of accountability.  Most sponsors joyfully embrace this role and effectively drive accountability across the team and with the PM.  The PM has a specific responsibility to embrace the accountability, demonstrate respect for the sponsor with the project team, and cascade the accountability throughout the project team.  Too often project managers will bad-mouth the sponsor to the project team and undermine his or her credibility as sponsor which creates ill-will between the sponsor and the team.  The sponsor needs to drive objective accountability and the PM needs to demonstrate respect and ensure all team members are held appropriately accountable for results.

Truth #6: Great sponsors are on top of the big issues and stand at the ready to help resolve them. Great PM’s articulate issues clearly and timely and escalate only those they can’t solve.  Too many times in my career I've seen a project sponsor be treated as if they were royalty.  The PM would make the trek up the mountain to report progress to the sponsor in hopes of pleasing him or her and getting a nod of approval from his or her highness.  Here's the reality:  the best sponsor/PM relationships are when both the sponsor and PM recognize the sponsor plays a specific role on the project and fills needs that he or she is best suited to fill.  The sponsor needs to be on top of the big issues which are appropriate for him or her to be addressing and be "at the ready" when the team needs an issue to be addressed.  At the same time, the PM needs to make sure that only those issues which are appropriate for the sponsor to address are being escalated.  Too often the PM will use issue escalation either as a means of "covering your butt" thus putting the sponsor on notice for an issue or will escalate inappropriate issues due to flat-out laziness.  The PM needs to escalate only those which cannot be solved at his or her level and ensure the sponsor is given as much time as reasonable to put the issue to bed.  The sponsor needs to be ready and willing to act. 

Truth #7: Great sponsors are an advocate, coach and battering ram for the project. Great PM’s know how to leverage a sponsor and listen to the sponsor’s counsel.  Some of the best sponsors I've worked with provide an open door to coach and counsel the PM.  The sponsor shows an active interest in the PM's success and deliberately works to help the PM grow as a professional.  They also serve as an ambassador for the project to other areas of the organization to ensure other stakeholders and constituents are supportive of the project.  Their interest is much more holistic and strategic; they want to help the organization be better and help the PM be better at his or her job.  At the same time, the best PM's see this relationship as an opportunity to grow personally and professionally and actively seek out and listen to a sponsor's coaching.

Truth #8: Great sponsors willingly make tough decisions even if unpopular or politically charged. Great PM’s provide clear and unbiased alternatives, information and consequences to support decision making.  On virtually every project there will be at least one decision which the sponsor has to make which will be unpopular with some organizational faction.  The PM has a clear responsibility to provide the sponsor with an objective point of view on decision alternatives, allow the sponsor as much time as reasonable to make the decision, and, while being politically aware of consequences, not be politically driven by consequences.  The sponsor needs to ensure alternatives are appropriately vetted, the facts and consequences are understood, and then make the decision as timely as reasonable.  The PM needs to be believable and objective, the sponsor needs to be courageous and timely.

Truth #9: Great sponsors don’t opportunistically increase scope if the project is going well. Great PM’s keep the team focused on delivery and don’t claim victory too soon.  In the 2006 Olympics, snowboarder Lindsey Jacobellis had the gold medal all but won. On the last jump of her race Lindsey does a hot dog move and trips at the finish line only to walk away with the silver medal.  Victory was in sight, cockiness crept in, then something bad happened to blow it.  Projects are no different.  The sponsor and PM need to jointly ensure that victory doesn't get claimed too soon, that scope control doesn't get sloppy, and that the team stays focused on driving the project to conclusion.  The sponsor needs to resist the desire to add "just a little feature" at the end and the PM needs to not allow the team to relax. 

Truth #10: Great sponsors continually evaluate priorities and are willing to pull the plug on a project if it no longer makes sense to do. Great PM’s don’t get emotionally tied to a project and don’t lobby to keep it alive if it should stop.  Sometimes a project no longer makes sense to do.  Whether it be about changing priorities, overly aggressive benefit statements, or under-estimated costs, both the sponsor and PM need to keep an ear to the railroad tracks and ensure the project still makes sense to continue.  If the sponsor has bigger fish to fry he or she needs to either continue to commit to the project or kill it.  The worst thing a sponsor can do is allow a project to die a slow death due to disinterest.  It not only wastes time and money but also creates disillusionment with the team because management isn't demonstrating support.  The PM needs to keep a "business first" attitude and recognize that sometimes a well-intentioned project no longer makes good business sense to continue.  Lobbying to keep a low-priority project going will just delay the inevitable.

The project sponsor/project manager relationship doesn't have to be contentious or stressful. When both are rowing in the same direction it can greatly reduce friction on on projects and make for more effective execution. Take the time to build the partnership.