One of the best places for many new entrepreneurs to start is SCORE. (Disclaimer: WorkingPoint is a SCORE sponsor.) SCORE is an organization comprised of small business owners — some actively running businesses, others retired — who work together to build a community to support other small business owners.  While some parts of the country have locally grown networks to support entrepreneurs, SCORE has more than 350 chapters across the US, dedicated to providing counseling and advising services to small business owners.

This week, on SCORE’s Ask an Expert blog, advisor Steve Bloom posted an article on a recent experience he had working with an entrepreneur whose idea was not something he felt had sufficient market to be a viable business.  In the post, Steve recounts the conflict he felt between wanting to encourage the entrepreneurial spirit and the strong sense that this particular idea had extremely long odds of success.

Ultimately, the real point he endevours to drive home, is that whether or not the idea is successful, the entrepreneur can still learn a tremendous amount from trying to get his venture up and running.  The value of the lessons one can learn through failure is something that every entrepreneur must always remember.  In the blogosphere “failing fast” is a common topic, but in reality, most of us are so terrified to fail that we will often turn ourselves inside out in an effort to avoid that experience.

This is one of the places that a mentor can help: a mentor who has been through the process before can not only offer their insight and perspective to help navigate pitfalls, but they can also help remind you that, even in the event of failure, you still get value out of an experience.

One of the most important exercises one of my earliest mentors walked me through was a process of defining my ‘worst case scenario.’  And, amazingly enough, I quickly realized that once I defined my biggest nightmare, it wasn’t anywhere near as scary as it was when it was a nebulous, ill-defined gray cloud hanging over my head; even better, it became much easier to insulate myself from the worst of the possible ramifications once I was clear about the details.

The flip side of Steve’s lesson is equally important: a mentor does not know everything.  And while it’s always nice to have a mentor who understands both you and your idea, the fact is that everyone has different strengths.  Just because a mentor may not consider your venture to be the world’s greatest idea, doesn’t mean it isn’t worth doing.

Part of the test for a mentor is to give you the best advice and encouragement they can; part of the test for an entrepreneur is to listen, process the information, and then make a final determination based on what you know to be true.  You won’t always agree, but that doesn’t make the advice bad, or the mentor wrong.  And hearing those concerns raised is always important, because it helps a new entrepreneur re-examine assumptions and ideas, to make sure there are no holes that have been over-looked.

So, if you have or are looking to start a business, and you do not already have a mentor, I’d strongly recommend looking for one.  There are plenty of different approaches to try (serial entrepreneur Penelope Trunk isn’t above being slightly annoying to snag the one she wants), but whatever you do, start looking for one — check out a local SCORE chapter, Chamber of Commerce, startup incubator or entrepreneurial Meetup.

Wherever you look, just remember: someone who has done it before, always has insights of value for someone just starting out.  They may not all fit, but there is always the chance for some great gems that can help you side-step a landmine.

This post originally appeared as part of my Entrepreneur Evangelist series on WorkingPoint‘s Small Business Blog.

But every startup hits a tipping point, and it’s rarely articulated as clearly and beautifully as Steve Blank does in an article posted to VentureBeat today. The transition from a ‘scrappy startup’ to a mid-sized company trying to be more mature is always infinitely more painful a process than anyone seems to think is reasonable.

This surprises me every time I see it. In his story, Steve recounts watching a new CFO to a mid-sized firm implement a ‘no more free soda’ policy and inadvertently spark an exodus of the founding team of engineers. What’s more interesting, though, is that some of the comments posted on the story miss the point: the engineers didn’t leave the company because the company started charging them $.50 for a Coke. The engineers left because being charged $.50 for a Coke was a sign that the company was no longer the same organization that they’d previously been willing to sacrifice for.

That’s a subtle distinction, but a vital one. More than once, I and many of my colleagues, have been willing to take significant pay cuts to work in environments that had a culture (or other intangibles) that made the trade-off worthwhile. Eventually, though, most organizations change enough to where that trade-off ceases to be worth it. The part that is often upsetting, however, is that those changes are frequently sparked by someone coming in the door more intent on shaking things up than on understanding the culture they are walking into.

Steve’s story is one that I can relate to over and over again. It wasn’t until I had a truly remarkable executive come into our organization, and refuse to act precipitously, but instead insist on watching and interviewing the entire staff for his first 60 days, that I had the slightest hope of someone making positive changes without unraveling the cultural elements that held us together, even in the face of the chaos. So now, when I go into startups, many of which are at the transition point between early-stage/founding team, and their second generation, I have a five step approach I follow:

1. Recognize that, for founding teams, everything is personal. The people who build a new organization take on a lot of risk and chaos to do it. They have to believe in it. It’s almost a religious experience, and you can’t come in a year or two later and expect them not to take your changes personally. Because, whether it makes sense to you or not, everything is personal. They’ve sacrificed too much for it not to be.
2. Understand the evolution. You have to be a bit of an archaeologist when you go into a new business. Do not make assumptions about how they got where they are. If you look long and hard enough, talk to enough people, and do your research, you’ll find that even the craziest things you see have a reason for having evolved the way they did. Unless or until you understand that reason, anything you do to try to “fix” the situation runs the risk of alienating people unnecessarily.
3. Respect the sacrifices made by the people who came before you. Unless you know that the people who are there when you walk in the door are dead wood and you want them to quit, make sure you demonstrate some respect to what they were able to accomplish — especially if they did it under tough circumstances. The single biggest source of alienation I have ever seen has been when new people come in, hot-to-trot, making changes and the people who built the company in the first place are treated like morons who simply got lucky.
4. Work on depersonalizing the business. It is reasonable that early stage startups are often personal sacrifices for people — they need to be. But a maturing company has to pass the point where that is no longer true. Not all of the early stage team will be able to handle that transition, but many of them can and will if they do not feel kicked in the teeth by new leadership brought in from the outside. Slowly building in an ethic of, “It’s not personal, but this is where the business needs to go now” is actually often much easier than people assume it to be. Founding teams want the business to be successful. That was the whole point for their sacrifice. If you want or need them to stick around, then help them learn to take a step back and not see the evolution of the business as an emotional affair.
5. Facilitate relationships between the old guard and new guard. Not all of the old guard is (or should) make the transition to the new phase of the business. And not all of the new guard is capable of showing any respect for what the old guard has done. But if you focus on individuals, their talents, and understanding what drives them, it is often possible to help connect people in ways that build strong teams to move the company forward. But you must keep in mind that there is often an automatic lack of trust between both groups, a tendency to point fingers, and a common tradition of resentment that you must work through before you are going to see progress.

Businesses are made up of people. And not every person is right for every business at every stage. Some really do need to move on as an organization grows. But that should be a deliberate, well-considered decision, not a haphazard, expensive mistake spurred by a short-sighted, penny-pinching reason. Unfortunately, that’s the cause I’ve seen most frequently throughout my career. And it’s a bit tragic, because a lot of dynamic organizations have lost a lot of amazing talent that could have helped grow the business and make it successful.

(This post is part of my Entrepreneur Evangelist series and was originally published on WorkingPoint‘s Small Business Blog.)

What is more motivating than traditional ‘incentive’ packages?

• Autonomy
• Mastery
• Purpose

The new “operating system” for business.

The single biggest issue I find when I come into an organization to help get things back on-track, is that when leaders are entirely pre-occupied with a strategic vision, there is a tendency to ignore employee development and management activities.

The irony, of course, is that a good strategist understands that employees are the key to making their strategic vision come to life. Yet time and time again, I have found that groups with the most strategically-focused leaders are the ones where the employees are the most neglected.

The problem, I believe, is in the misalignment of how a leader identifies — and what they actually like to do — versus what is part of the responsibility of the role. How many people who consider themselves innovators, visionaries and strategists are placed in the role of manager? And, honestly, much about managing people is terribly “innovative”? Very little of it. Managing people is down-n-dirty work.

Someone who manages people has to deal with messy details like:

• team members who don’t get along
• people who are not living up to expectations
• talented people who are bored thanks to being under utilized
• political entanglements with other departments
• hiring freezes that prevent backfilling vacated positions
• low morale among teams
• budgetary constraints that prevent a manager from paying an employee what they are truly worth
• helping form a career development plan so team members don’t stagnate
• being honest with a staff member when there is no future for them with the organization

Face it, none of that is sexy. But someone who can’t or won’t do those things is not someone who should be managing people. And yet it happens all the time: a strategically oriented leader is put in the role of a manager, because leadership likes the idea of having a strong strategic direction developed for the department.

Nothing wrong with that. Of course the best departments are marching towards a strategic vision. But if you don’t take care of your team in the process, who exactly is doing the marching?

Between getting settled into the new project and speaking to old friends at former companies (some of whom are now unemployed, while others only wished they were), I’ve been thinking about a number of things that seem to have dovetailed together in a way I wasn’t expecting.

First and foremost is career management. Long a favorite topic of mine, what I’ve been thinking of recently is how sadly common it is for a boss to be totally useless when it comes to helping their employees with career management plans. More than a few of them don’t think it’s part of their responsibility (which I find inexcusably lazy), but even more of them seem to simply not think of it.

This got me thinking of the series I wrote at Christmas, “A Christmas Card to My Bosses: Thanks to Three Very Wise Men.” While I wrote blog posts on the great lessons I learned from each John, Robert and Dave, the thing that I didn’t state explicitly (but which was implicit) was that each of them cared about and was focused on making sure the people on their staff were getting the career development support, encouragement and pushing that they needed. They were all acutely aware of the role they played in developing their people; they took that responsibility seriously and they executed against that.

I see so many talented people who do not have that. And when they finally have someone actually demonstrate some interest and some focus on helping them define and reach their career objectives, they are often so stunned they can hardly believe it.

Why is it so hard? Most people who have been successful enough to be the boss have accomplished that because they know how to manage their own career, so why is it so hard for them to help give guidance and advice to someone else on how to do the same? It shouldn’t be — and I don’t buy that it usually is. I think the reason most people don’t do it is because they don’t make time to do it.

An important thing to keep in mind: statistically speaking, most people do not leave their job, they leave their boss. So are you doing what you need to do to keep your employees engaged and supported so that they stick around? If not, why not?

So that’s my challenge to bosses everywhere: have you worked with each of your direct reports to make sure you understand their career goals (at least as much as they do)? Have you worked on a plan for them that will help them make progress towards those goals? Are you checking in with them regularly to make sure that they are staying focused on at least some of the accomplishments they need in order to stay on track?

Part of being a leader is helping make sure the people you are leading are getting where they need to go. If you aren’t doing that, then where are you leading them?

Specifically, I’ve been thinking about how early career choices can really set the stage for the directions we take in life. As is often the case, many of the largest influences on our lives are not obvious until many years later. And while I am as likely as anyone to take them for granted, every once in a while something will happen to make me stop and consider the series of events that brought me to where I am now, and what the unintended consquences of seemingly small actions or events have ultimately provided.

There were three defining elements of my early career that I have been noodling on, because they had much larger impacts on me than I ever would have predicted at the time:

• Getting your start in a startup. What is the value to launching a career in a startup environment?
• Being in the ‘wild west’ of a new market space. What does it mean to be in a new space?
• Transforming a company from being “a services company” to “a product company.” What are the differences and why are they important?

Undoubtedly, the first two of those are a bit sexier than the third. However, all three ultimately shaped me in ways I never fully realized at the time. The lessons learned were a bit rough sometimes, but when I compare some of my experience to that of my peers, I realize that I had the opportunity to be involved in some things that have served me extremely well and that I wouldn’t trade in for anything.

Over the next couple of days, I’ll cover each of these topics in a separate post (each one is too long to combine them).

Conversely, a dear friend who is in the process of developing a business from a one-man shop to a full-scale product company, disagrees strongly. While he has never been an advocate for ‘butts in chairs’ as an organizing model in general, he definitely doesn’t subscribe to the idea that the people you would pull together to get a business started can’t do what they need to do virtually. If someone is good enough for you to enlist to help get a business off the ground, then they should be talented enough to do what they need to do remotely, while communicating with the rest of the team in an effective manner.

However, he does admit to a single hurdle that will quickly need a solution: team-building — which ultimately leads to organizing models and culture.

In the most immediate term, the easiest way around this is for the people working together to found the company to already know each other. If those in the trenches to get it off the ground have worked together in the past, have long-standing relationships (both personal and professional, ideally), and respect each other’s abilities, then it there is a foundation of mutual trust that helps get the ball rolling.

But there are still obstacles with that, even among people with common work histories and mutual trust.

What is everyone doing?

This is the area where newer organizations, if they implement some basic technology solutions in the beginning, can really set a strong precedent for organizational transparency. Enterprise 2.0 has some great capabilities when it comes to finding ways for people to have a transparent audit-trail of their day, that can be visible to everyone.

What code did your developer fix? What are the status of the bugs? How many phone calls did your salesperson make? What is the state of the new partner contract? Has there been any performance degradation today? Which client just requested a new project? Almost all areas of a business can be supported by tools that have standard out-put capabilities (such as RSS), which can be aggregated centrally so that an entire, geographically distributed team can see what is going on in everyone else’s corner of the business.

For some people this is a bit on the creepy ‘big brother’ side. I’ll concede that I can understand why. But this is where the reason for it is important, and where the cultural element is critical: this is about building a culture of transparency, not a culture of mistrust. The “how” and the “why” make all the difference when it comes to the “what.”

If leadership were excluded from this type of transparent work tracking, then it would be easy to argue ‘big brother.’ But the idea is that this starts with an organization’s leadership. They are leading the way by ensuring that their activities are truly transparent.

So much of the Enterprise 2.0 sector is focused on transforming established businesses into transparent and collaborative environments that we don’t spend a lot of time discussing the first rule of building something new: lay the right foundation to begin with, and you can build whatever you want on top of it.

Penelope Trunk made a great point when we spoke: the technology a business chooses to implement speaks to their culture and their values. She is right. Businesses getting started today have almost no technical or financial excuse for not leveraging some great technical solutions — all of which can help reinforce some essential cultural values — to get work done. Cloud computing and SaaS (often freemium) solutions are too pervasive.

If you want your team to collaborate, set up a wiki. If you want feed everyone’s activities for the day into a centralize spot and can’t afford to buy a solution yet, use Yahoo! Pipes. If you want a centralized dashboard that everyone can access easily, use Google Apps. If you’re totally overwhelmed and have no idea what you need, check out Zoho or one of Mashable’s infamous and extremely helpful lists. There are plenty of solutions, most of them with free (or at least very low cost) options. And if you start off using them from day one, they will become part of everyone’s routine and you can skip the painful change management efforts that come with trying alter everyone’s behavior down the line.

Blowing Off Steam, Celebrating and Bonding

Ultimately, the truly hard part about having a virtual team is that there is a certain degree of bonding that really just requires face-to-face interaction. This is where it is most helpful if your virtual team isn’t so far apart as to preclude semi-regular face-time with each other (i.e. if the team is scattered around the Bay Area, but can meet for long lunches/working sessions every couple of weeks at a centralized location). However, sometimes this simply isn’t possible, and the team is a couple thousand miles away (or more). This is where you have a real challenge.

The strongest bonds I’ve ever forged with co-workers — and the point at which co-workers really started becoming true friends — were always a result of bonding under extremely stressful circumstances. It’s the ‘war buddies’ syndrome. You always learn the most about people when you put them under true pressure. And the bonds that form between people under those conditions are commonly very strong. But more often than not, they are strongest when everyone is in the same room.

So how do you truly build a cohesive, trusting, bonded team when everyone is dialed in on an ooVoo conference call from their home office? Particularly once the company starts growing a bit, and it is no longer 2-4 people who all already know each other, how do you start adding in more of the expertise you need without adversely impacting the group dynamic?

This is an on-going source of debate and speculation. Most of the more robust and well-tested virtual team-building models are based around taking formerly co-located teams and re-distributing them (think IBM giving up office space and sending their employees to work from their home offices). So while a quick Google search on “virtual team building” comes up with a host of plausible hits, in the end, most of them are variations on cheesy in-person team building exercises that I rarely find all that effective.

As VC funding continues to dry up, and small startups are forced to do more bootstrapping, geographically distributed companies are going to become increasingly common simply because office space is too expensive and people can’t afford to pick up and move for a low-paying/high-risk startup role. That is going to force a lot of experimentation in this are, and many of these models will have to be developed.

Of course, odds are that my friend’s model will be a common one: if you are going to roll the dice on a new business, it usually feels like a safer bet doing it with someone you not only know, but someone you know you can work with. So, as with many other things about a small startup, you can get away with certain short-cuts in the early days that you have to keep an eye on, because they rarely scale the way you need them to, and if you aren’t paying attention, they’ll come back and bite you before you know it.

Naturally, difficult economic conditions demand a re-evaluation of spending habits. And, in cases where projects are reasonably small, there are very few stakeholders involved and requirements are very straight-forward, I would never argue that project management should be full-time. I am a firm believer in the value of tailoring the project management process to meet the needs of both the project complexity and the organizational maturity. So there are absolutely times when doubling up on roles makes sense.

However, before you decide to swap out the PMPs for the Developers with decent leadership skills, consider the following five questions carefully:

1. Who are the (non-project team) stakeholders for this project?
This is one of the most important questions to consider. If your “project sponsor” is your Director of Engineering, then maybe having the development lead function as the project manager makes sense. After all, presumably they already have a standing working relationship, comperable communication styles and are often coming from a similar view point in crafting a solution.

But what if your stakeholders are not technical people, but non-technical business clients (either internal or external)? Is your development lead the best person to communicate with non-technical project stakeholders about things like status, risks, issues and process implications? Is it good for the project’s outcome for the development lead to spend several hours of his week in business meetings in which decisions are debated or designs are evaluated, instead of leading the technical team in matters of architecture and design?

2. What technical disciplines need to be involved for this project to be successful?
It is rare for any project to be exclusively a development effort. Most technical projects also require DBA, server, network and QA resources; additional ones such as design and documentation can also be critical, depending on the project. A common problem in having a project managed by a developer is the tendency for a natural bias towards application development at the exclusion of the other technical aspects of a project. And even when the development lead is actually unbiased, it is not uncommon for organizational politics to foster an illusion of bias from the point of view of other technical team members. A project manager often has an easier time being perceived as unbiased, and therefore establishing mutual trust and team cohesion.

3. What are the finances for this project?
Does your organization track specific department and/or project budgets? Or are you operating in a ‘slush fund’ organization that doesn’t clearly delineate one department’s budget from another department’s budget? If so, then maybe cost management isn’t a huge deal and internal projects can be allowed enough leeway that managing to a budget isn’t a primary concern. Or is yours a sales-driven organization that is running client projects on a time and materials basis? If so, then there is no way that cost management isn’t a huge element of successfully delivering the project to ensure that the client doesn’t have a rude awakening with a bill they were unprepared for or your organization doesn’t find itself eating unexpected costs because a project was allowed to careen out of control.

4. What is the level of technical complexity of the solution being implemented?
This is one of the most dangerous questions, because it has been my experience that developers are often highly optimistic people when it comes to estimating both technical complexity and time needed to implement a solution. As such, one of the single most common mistakes I have seen repeatedly occur in projects led by developers is a tendency to underestimate both the technical difficulty (particularly when it comes to what non-dev technical resources will be required: servers, network configurations, etc.) and the amount of time needed to make it work. While I applaud the nearly universal ‘can do!’ attitude of almost every developer I have ever worked with, one of the principle functions of a good project manager is to protect the team from overly ambitious (if not out-right unrealistic) timelines and expectations. And, truth be told, often times one of the most important things a PM does to that end, is to push back on team members who give simple, shiny answers to technical questions that are long on optimism and short on details.

5. Is there any outside procurement of goods or services needed for this project to be successful?
Again, if this is a fairly small project that can be successfully accomplished with the people and resources you already have within your organization, then great. That should help simplify a number of things. But as soon as you start needing to look outside of your immediate team for any goods or services — servers, third-party applications, consulting services, new business partners, etc. — you are opening up a whole huge can of worms. Drafting RFPs, evaluation RFP responses, selecting vendors, negotiating contracts, managing vendors, monitoring financials/billing and more are part of the endless fun and excitement of procurment. Is this something that your development lead is ready to do? Or, even more importantly, is this something your development lead has the time to do and still deliver the code on time?

Project Managers are not over-paid admins. There is a lot of work involved in successfully delivering a project and meeting the expectations of stakeholders. Per PMI, Project Manager’s spend 90% of their time communicating — with sponsors, with team members, with clients, with finance, with functional managers, etc. The best project managers tend to be extroverts; and the best developers tend to be introverts. Each role has different needs and therefore attracts different types of people; it is rare that one person is very good at both.

But even assuming for a second that you have a development lead who is a strong communicator and who understands the integration challenges of successfully launching a project (and I have met plenty of very talented developers in my career, and any number of them had the skill set and desire to be perfectly good project managers), if they are also expected to function as a development lead on a project, all the skills in the world don’t make up for the one thing they need and do not have: TIME to do both jobs.

Be wary of falling into a trap of being ‘penny wise and pound foolish’ when it comes to staffing your projects. Expecting that a development lead is going to have the bandwidth to fully manage all critical aspects of a project and still be able to lead development efforts is a dangerous gamble. And one that rarely pays off.

But before I get started on the specific men and the specific lessons they taught me (and yes, my list is entirely male), I figured I’d take a moment and try to define what I think makes a good boss.

Political Savvy
The best bosses are always the ones with, as I like to call it, ‘great sea legs.’ They are the people you can bring into a new environment, and they are socially and politically savvy enough that it takes them almost no time to find their balance and then successfully navigate the sometimes treacherous waters of office politics.

These are the bosses who not only roll with the punches as business conditions change, but they are also the ones who show you how to adapt and change what you are doing to be most successful because of it.

One of the greatest examples was monthly executive status reporting I was doing at one company. Our team had spent several months fleshing out the set of reports we were presenting every month to the executive to whom our department reported. The reports were geared to focus on the things that this particular executive cared about due to the nature of his role. As soon as we were moved to another spot on the org change, my boss and I worked together to re-define what those monthly reports needed to reflect, now that our executive leader was someone else, whose interest was in completely different areas.

A politically savvy leader knows when to push and when to back off; what battles to fight and which ones to let go. Without having a fundamental understanding of these things, long-term success is nearly impossible. Another common buzzphrase for this kind of self-aware, political astuteness and contextual sensitivity is emotional intelligence.

Inquisitive
A great boss asks questions — the most important two being, “Do you need anything?” and “What is it that you really want to be doing?” — and they internalize the answers.

A good boss should understand what you love about your job, and what parts of it you’d love to avoid if you could. He knows where your biggest areas of growth are, and where your biggest strengths are. He knows what you want out of your career, and where you’d like to see yourself down the road. But he knows those things because he’s asked.

(And, in all fairness, if you either do not answer or do not try to find the answers, then you aren’t doing your part to meet your boss half-way so that he can actually be a truly good boss. A good boss/employee relationship is a two-way street, and neither side can do it well if the other side is disengaged.)

“A Teachable Point of View”
To swipe the phrase from Noel Tichy, “great leaders are great
teachers.” Their underlying philosophy, the foundation for their decision-making paradigm, needs to be established and it needs to be teachable to those around them. A boss whose management style and leadership philosophy changes weekly based on the most recent book he’s read, or a leader whose solid philosophies about managing are closely guarded secrets will never be great bosses. Ever.

In order to be a great boss, you have to have both the content and desire to teach. And you need to make it a priority.

Without a doubt, every boss I’ve ever seen who demonstrates these qualities not only fosters high performance teams, but also breeds a deep respect and fierce loyalty among his staff. Among the bosses I’ve had who have demonstrated these qualities, some have been introverts, some have been extroverts; some have been C-level executives, while others have been managers; some have come from large, mature organizations, others have come from entrepreneurial startup environments. They have all had very different temperaments, personalities, senses of humor and habits (both good and bad).

But they have had two vital things in common: the above listed qualities and the fact that, whether they knew it at the time or not, they each made a huge impact on my life. So this is my Christmas card to three men from whom I learned more than I ever expected, and whose lessons impact business decisions I make daily.

• John, who taught me the value of being invested in your people.
• Robert, who taught me about the importance of owning your priorities.
• Dave, who taught me how essential it is to keep things transactional and not get emotional.

Merry Christmas, gentlemen.

And then she said it: what she was really angsting about was telling her mentor, who also happened to be her boss. And she was seeking my input specifically because he also used to be mine.

The entire conversation got me thinking: twice in my career I have had amazing mentors who also happened to be my boss. In both cases that was a great combo because it meant lots of access, tons of opportunity to learn in practical settings, lots of hands-on collaboration and great platform on which to build a really strong relationship. However, in my case, there was also one very serious downside in both cases — and it wasn’t as much about them as it was about me, and it’s one that I see in my friend now, and in other people over the years (including at least one person for whom I was the boss/mentor): when your boss is your mentor, it’s easy to stay at a job for too long out of fear of letting your mentor down.

In hindsight it is very clear to me that both times my boss was my main mentor, I stayed at a company long after I should have left — which caused a series of secondary problems I didn’t foresee. But hindsight also makes the “why” very clear: I didn’t want to let down my mentor, who was in the habit of counting on me, just as much as I was in the habit of counting on him.

In speaking to my friend, I outlined an approach to what is ultimately a difficult conversation to begin. (Dr. Lois Frankel has written about this issue as well, particularly for women who have a very father/daughter type of relationship dynamic with their mentors.)

1.) Be first and be direct.
Don’t let your mentor hear the news from someone else. In order for a mentor to be a mentor, he needs to know what is important to you, what your goals are and what you’re thinking. A mentor who doesn’t know that your long-term goal is to be CIO or that you’re hoping to move across the country is not in a position to be a good mentor to you; and if you don’t share that information with him, then any decision to make to achieve any of your big picture goals is always going to come as a surprise.

And definitely do not let your mentor hear the news from someone else — this is a particular danger if your new role is within the same company. A new boss is almost always going to talk to your current boss (most companies require it as part of an interdepartmental interview process), and if your mentor gets ambushed with the information from someone else, it’s going to make things very awkward for you to talk to him later. It’s also a disrespectful thing to do to someone whose opinion and respect you supposedly value.

2.) Be rational about your reasons.
This one can sometimes seem harder than it really is, especially if your reasons do not appear rational on the surface. For instance, if you suddenly find that half your department is being outsourced, but you are safe, then it can appear that electing to leave yourself is strictly emotional and unnecessary. But that’s not necessarily true at all. In a world of constant IT outsourcing, being one of the handful of remaining professionals in the ghost town of what was formerly a large technology organization is a rough gig. Watching your friends and colleagues leave, riding out what is a difficult transition period, witnessing the evaporation of the organizational culture and still getting your work done in and among all of that chaos is extremely difficult to do. The argument that, “At least you still have a job!” is not invalid, but it’s also not the whole story. If part of your reason for leaving is that the existing situation is so impactful to morale (including your own) that you are finding productivity to be increasingly impossible, then that is a rational argument for leaving.

Other good reasons for leaving include one of the biggest ones of all: opportunity for growth. Your mentor should be very clear about your long term goals (at least as clear as you are). And any mentor worth their salt (and your loyalty) should be helping you meet the goals necessary to achieve those ends. A good mentor should also recognize when he can’t provide you with as much opportunity as you can find somewhere else. But when you speak to him, be prepared to outline the reasons you feel the new opportunity offers you more than your current role does. A good mentor may question, clarify or offer suggestions you haven’t considered, but he should never, ever dismiss your opportunities for growth or progress as unimportant.

3.) Be prepared for an emotional response, just in case.
People are people, and as much as you may be dreading telling your mentor, your mentor could have a hard time hearing that you are leaving (especially if he didn’t see it coming). This is often especially difficult news when he has come to depend on you to handle something particularly big/nasty/difficult so well that he doesn’t have to worry about it and can focus on other things.

If you know your mentor well enough, you will probably have a good idea what an emotional reaction is likely to look like: Angry? Disappointed? A guilt trip? A counter-offer? Whatever tact is most likely, have a counter-card ready to play in case it is necessary.

If your mentor is likely to get passive-aggressive and toss a bit of a guilt trip at you when he is upset/surprised, then you have two choices: find a guilt trip you can toss back out at him in the moment if necessary; or be prepared to point out that he is getting emotional and attempting to guilt you (most people don’t necessarily realize they are doing it in the moment, so you can often put a quick stop to it this way if the person does truly care about you).

With some people it’s best to match them quid pro quo rather than to potentially embarrass them by pointing out that they are being petulant and unfair. It’s a little manipulative, but it saves face, which can sometimes go a long way towards maintaining a strong relationship after you’ve departed. So being prepared to toss some guilt back his way if he tries to guilt you into staying is often a way of getting him to back down without overtly taking a pie in the face. Guilt can also work well if his inclination is to get angry; handled correctly, you can diffuse him a bit by making him realize he’s being a bit of a bully.

4.) Be grateful.
If your boss is your mentor it’s because he has made investments in you — financial as well as emotional. And the reason you feel conflicted about leaving is because you are grateful for everything that he has done and do not want to disappoint him. But, as is the case with most daily relationships, we rarely tell the people who matter most in our lives how we feel. So take this opportunity to thank him for everything he’s done and everything you’ve learned; point out to him that the lessons he’s taught you have been valuable and that this new opportunity offers you the chance to apply those in a new setting and further develop your skill set. The “I am only in a position to take on this new challenge because of what I’ve learned from you” argument serves the dual purpose of being both effective and true, so take advantage of it.

Of course, the fact is that people are human and if your boss is your mentor then he should care about you and want what is best for you. One of the things you may have to brace yourself for is that your boss could be consumed enough with his own problems that he has some trouble being gracious about you needing to do what you need to do for yourself, especially when it has the unintentional and unfortunate side effect of making his life more difficult in the short term. But, once again, if your boss really is a mentor, then once he has some time to process through your news (and your reasons), he’s likely to come around. You may just need to be prepared to give him some time before you can expect a lot of sincere congratulations on your new job.