Think about your normal daily experience: if you need to deal with your bank, your insurance company or your utility provider, you call an 800 number, where you are greeted with an automated message, a phone tree that routes you through a series of menus, as much automated information as they can possibly prepare, and then — if you’re problem is too complicated to automate — eventually you may get a person.

And then what happens?

You have to repeat your account number, despite having entered it already (at least once); you have to answer questions to validate your identity (or, worse yet, you don’t, which always begs the question: who else can get into my account?); and then you can get around to your question.

In many cases, by the time you get to speak to a real person you are dealing with a call center on the other side of the planet, non-native speakers (who sometimes struggle mightily with English), and in worst case scenarios, people who are clearly reading from a script with very little real understanding of either the nature of your problem or how best to handle it.

And when it’s all said and done, how often do you go through all of that, and get off the phone feeling totally confident that your issue was resolved? Rarely. More often than not, most of us get off the phone feeling like we just got the run around so badly that we need to double and triple check our next round of statements to make sure no one messed anything up.

All in all, because of the economic needs for businesses to automate and off-shore customer service functions, the general state of Customer Service is often crap.

This is where small business owners can be Superman. Seriously. For most small businesses, we don’t have the volume to go through all of that expense and hassle. Our customers often have our direct phone number. They know where to find us, how to reach us and what our specialty is. And while that may not always be great for our daily productivity (and it can certainly be abused at times), it gives small business owners the chance to leave our customers with a far, far better customer service experience than the one they just had with their credit card company.

We talk so much about business that we often over-look the most important fact of all: business is conducted between two or more PEOPLE. Sure, there are functions that can be automated and there are often good reasons to do it. But when you leave your customer feeling like less than an actual person, you’ve just provided a lousy customer service experience. Small businesses, because of logistics, have a built-in advantage. And it’s one we should all remember to take advantage of.

For some people, this is easy.  Moving ahead, pulling the trigger, motivating people into action, moving at light speed — categorize it however you like, but how comfortable you are with this type of thing often starts out as being a very basic part of your personality.

For other people, however, this is much, much harder.  Whether it’s a fear of being wrong, a need to collect input from numerous different sources, or just a methodical decision-making process, some people are very uncomfortable churning through a couple of dozen decisions per day, and tap-dancing their way around obstacles in real time.

So what do you do if you want to own your own business, but rapid-fire decision-making did not come baked into your DNA?  Here are a few tips and tricks I use when working with new entrepreneurs, to start getting them comfortable with what the role demands of them:

Define and document your process
Everyone has a different process for making decisions.  But for most of us, it’s intuitive and has evolved over time.  We often don’t think about it, or even recognize all the steps.  The benefit of sitting down and writing it out (I often either recommend a flow chart or a bullet list) is that it helps us be aware of places we are likely to get stuck or where we become repetitious.

Focus on what your process actually is, not what you’d like it to be.  (You can work on changing it later.  Start off by understanding it.)

Even more valuable, however, is having this on hand when it comes to working with others.  Because if you can show your partner or your staff what your decision-making process looks like, it helps manage their expectations.  It also identifies at what point you need input, and at what point they need to be prepared for action.  It sounds amazingly simple, but it’s invariably far more powerful an exercise to go through than most people expect.

Once you’ve documented your process, the next step is to identify the part of the process with which you are least comfortable (generally speaking), and at which point in the process you most frequently find yourself getting stuck.  Sometimes it’s the same step, sometimes it’s not.  But again, breaking it down and really thinking about something that you do instinctively is critical if you are going to start changing your habits at all.

Partner up
For as nice an idea as it is that we are all always going to keep our promises to ourselves, the truth is, our promises to ourselves are often the first ones that we break.  So for most of us, accountability is most successful if it is to someone else entirely.  So find a parter, coach or collaborator.  It’s like having a workout partner for the gym: sometimes knowing that someone else is expecting you is the only way you’re going to make it.

Whether you go to an organization like SCORE for a mentor, or you hire a business coach, or even a part-time project manager to help you with planning and organization, sometimes the best thing you can do for your progress is to put yourself — and your money — on the line.  Putting some skin in the game is almost always good for the end results.

Break it into bite-sized pieces
Some projects and efforts are just huge, and until you dice and slice them, they are simply too overwhelming to make any real progress.  So break it down.  Again, this may require some outside help, but once you have your efforts broken down into logical chunks, it’s much easier to define tactical next steps for each piece, and then to show — and see — progress.

The best rule of thumb is to keep every piece to 8 hours (or a day’s) worth of work or less.  Don’t let anything get too big, and it’ll be much easier to stay focused.  If you’ve parsed out your steps into day-by-day sized pieces, then you will also often find that the difficult decisions that seem huge in their original state are also broken down into more readily managable sizes, making them easier and faster to resolve.

Not everyone is a natural born entrepreneur.  But there are tons of people who are willing to do the work to make the transition, including being ready to push themselves out of their comfort zone to get there.  There is nothing wrong with wanting to analyze details in more depth; just be aware of the fact that being wrong is ok, and that there are very few decisions that can’t be reversed if they really need to be later.

Often times it’s not possible to know for sure that an answer is right until you’ve explored the wrong one a bit.  But if it doesn’t come naturally to you, find some help.  There are lots of people who have been there and figured it out already.  Take advantage of their expertise and get their assistance building a system to help you make the transition you need.

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

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?

And then I got a job — that ultimately turned into a career — at a start-up. Pay dirt!

The transformation that sparked in me is still an endless source of amusement among my friends. It took me a while to realize why, but eventually it was clear: the problem with school is that there was an upper limit on what I was capable of achieving. It was an artificial cap on how well I could be scored. I found that inherently disincentivizing. In business, however, there is no upper limit. You can take something as far or as high as you can push it (given the right environment, of course).

And, even better, in a scrappy, entrepreneurial, risk-taking startup (especially one trying to survive an economic downturn) someone who is hungry, talented, teachable and willing to dive into the deep end of the pool head first has tremendous opportunity for growth. The first three years of my career were the most educational, exciting and energizing time of my life — all of my years of school combined couldn’t compare to those three years. Everything was new, everything was interesting and I never once had the slightest bit of doubt that I could conquer anything that came my way.

Ah, the hubris of youth!

Of course, there were downsides. Like many young people, I didn’t know my limits and was constantly pushing the envelope in ways that I probably shouldn’t have (and in ways that I’ve since learned not to do). Whereas many 26-year-olds may be more inclined to do that with parties, I did it with work. I ended up missing a lot of important events in the lives of friends and family because of that.

I was also still extremely idealistic about a great many things. Instead of The Pragmatic Contextualist, an appropriate blog title would have been something along the lines of The Snarky Idealist or Bring it On and Get Out of the Way! (Which, ironically, is still how some people tend to view me, though I have toned down considerably with age.)

But that idealism was invaluable to me, because it made me fearless: if anything is possible and I’m extremely capable, then what do I have to be afraid of? I don’t tend to be very risk-adverse in general, but I have become more cautious with age (though, not quite enough for either my husband or father’s tastes). Back then, though, it would never occur to me that I wouldn’t figure out a way to succeed at whatever I did — which meant I was a hopeless volunteer junkie.

My biggest rush came from fixing problems, and in a post-bubble burst start-up, there were plenty of things to be fixed. So I had an endless supply of opportunity, and endless confidence in my own success. Happily, I also had bosses who went from having nothing to lose by letting me try, to truly believing in my ability to make a positive difference.

As was inevitable, a few kicks in the teeth later, and I stopped being quite so cocky. The pragmatist in me was ultimately born of those experiences, and the eternal idealist retreated to the back, only to come out for the occasional political event.

One of the biggest, most valuable lessons I learned was how to deal with chaos. More recently in my career, I had a bizarre moment when a senior IT Director — who was easily 25 years older than me — groused that we were working in “the most chaotic environment” he’d ever experienced in his life.

I wanted to laugh and call him a weenie (I restrained myself — though barely). The environment we were working in at the time was easily the least chaotic environment I’d ever experienced, and his inability to roll with the punches made him a particularly weak and frustrating leader in my opinion, because he got frazzled very easily, whined constantly and was tremendously rigid. It never occurred to me until that moment that my ability to handle chaos was all that unique.

Naturally, one of the dangers of getting a bit too used to high volumes of chaos is that you can become a drama junkie. This did happen to me, and it took me a while (and outside circumstances) to curb it. But what I have seen of most drama junkies (and trust me, I wasn’t the only one I knew) is that, the older we get, the less tolerance we have for that same constant fever-pitch of insanity.

This is another reason that I have often recommended aimless twentysomethings seeking career advice to explore startups: because by the time people are settled in their career, married or have kids, startups can be a bit too rough on the lifestyle. So if you’re going to do them, best give them a shot while you’re young, energetic, single and have as few external obligations as possible.

But when I look back on that time now, I am profoundly grateful. I was drinking from a fire hose, and it never occurred to me there was any other way to work. I got to sample a spectrum of potential opportunities and figure out which ones held some appeal, and which ones didn’t. If I had found myself in a more stable, structured environment back then, I can’t imagine where I’d be now, because the lessons I learned there, and the all-you-can-eat-buffet of opportunities that I had available to me at the time are how I found my way into a career.

In the scheme of things, I look back on the most pivotal, impactful decisions of my life and the day I left the famed O’Reilly Publishing — which is where I thought I’d wanted to work for years — and went to MarketLive (at the time it was still called MultimediaLive) was one of them. And since then, I have found myself encouraging twentysomethings who do not know what they want out of a career to look at startups, because as long as they can develop a bit of tolerance for chaos (which I firmly believe everyone should do), they’ll usually find opportunities they never knew existed.

What do you think? Are startups a good or bad place to start out your career?

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).

That is, until we started talking in more detail. It suddenly occurred to me that, much like Krishna De‘s article yesterday about using blogs to attract customers, there needs to be more thought put into using blogs to service the customers you already have. “Engaging customers” is a wonderful buzz phrase, but there is real work behind those two little words. If you are not prepared for it, you could be in for a rude awakening.

As a compliment to Krishna’s questions, I would like to add the following three questions to the discussion: Who? What? …and How?

Who is going to be responsible for writing the content for the blog?

Is it the Marketing team? Or is it a cross-section of capable writers from other parts of the organization? Are the people doing the writing intimately familiar with your product line enough to speak to it in detail? Do they know the types of issues and challenges your customers face every day? And are they equipped or empowered to respond to those issues, if posted to the blog?

If we use a B2B or SaaS-type software company as our model, then I would recommend that writers from different parts of the organization are tapped to produce content that has a cross-section of relevancy:

• The Sales team can write great success stories of growth increases and wonderful ROIs.

• The Product Team can discuss little-used or new features; they can get feedback from customers on the newest releases and collect ideas to help prioritize future ones.
• The Design Team can offer tutorials to customers on good design practices, and usability considerations to keep in mind.
• The Implementation Team can provide suggestions and recommendations for the types of things that make a new implementation run smoothly.
• The Customer Service Team can help educate on the maintenance and upgrade process, on-going customizations capabilities and new feature training and applicability.
• The IT Operations Team can provide practical tips for good data security and can use the blog to speak to customers about routine maintenance windows or incident reports.
• The Quality Assurance Team can create a coaching series designed to help customers understand what the testing process looks like when they implement a customized project.
• The Marketing Team can provide tips designed to help your customer-base launch an effective marketing campaign – with either their customers or their employees.

The options are really endless, and this is precisely the type of information that often helps customers understand (and be more patient with) the process a company goes through to provide their services.

The last thing you want is for your Marketing Team to be trying to engage with your customers as though they are experts in all of these areas. Marketing people are experts in Marketing. Limiting your blog’s authorship to the Marketing Team only makes sense if what you are trying to engage your customers about is their marketing campaign.

A great example of a company blog that represents a broad spectrum of an organization’s disciplines is Convio‘s. Their blog, The Connection Cafe, is team blog – but not the Marketing Team. Their team is made up from people all across the organization, who work with clients in every different capacity throughout the client implementation life cycle. If you look at the Authors page, you’ll see the array of groups represented – starting with the CEO.

Not only does this provide article content that meets the needs and interests of clients at all different maturity levels and in all different stages of implementation, but it also keeps the blog from being monotonous to read and onerous to write. The Marketing Team owns the process, the writing standards, and the responsibility for ensuring that the content lives up to their guidelines, but they do not do all the writing.

What are you hoping to provide to your customers by engaging with them in the blogsphere?

This is a dangerous one, because all too often the answer to this question reveals that a company is less interested in having a “dialogue with” their customers than a “monologue at” their customers. And if that’s what you want, then skip the blog.

What is your organization’s relationship with your customers? Are they generally happy, or are they generally hostile? Do they feel like your organization is responsive to their needs? Or do they feel like once you’ve cashed their check, you’ve stopped caring about them?

Whatever the general consensus is among your clients, be prepared for the fact that if you get them to engage with you on the blog, that sentiment will be made very clear at every turn. And if you are not prepared for how to respond to it, then stop, count to ten, and figure out how you would before you move ahead.

There is very little that helps turn around troubled client relationships better than directness, honesty, and transparency. The only thing that works better is results. So if the team that is doing the blogging is completely disconnected from the teams who can solve the customers problems, then beware of setting everyone up for disappointment – and setting your customers up for a revolt.

It is not realistic to ask your customers to be involved in a dialogue if, as an organization, you are not committed and prepared to try to resolve (at least some of) their issues. But if the customer blog is completely removed from the operational planning of the organization, then you’re simply giving your customers a megaphone so they can scream into a well. And that’s just going to upset them more.

Do you know what type of functionality you really need in a blog yet?

It could be all of my years in small businesses and startups, but this one never ceases to amaze me: instead of starting small, with a local installation of WordPress, a company decides to spend a fortune on something written in a proprietary language – and this is all before they have any idea if their customers even have any interest in engaging with them via a blog.

Stop. Put the checkbook down. Back away.

I don’t care whether you call it a “beta” release or a proof of concept, but in these tight economic times, if there is one piece of advice I have for any Enterprise 2.0 evangelists out there, it is this: Don’t shoot yourself in the foot by asking for the moon unless you’re sure you really need it.

Times are tight. Budgets are being slashed. And ‘frivolities’ are frowned upon. While I would never classify a customer blog as a ‘frivolity,’ it is not uncommon that it is a hard sell to an executive with budgetary authority. Make your limited funds count.

Time and time again, we see that the organizations with the greatest success in Web 2.0 are the ones who are willing to experiment. But the only way to afford to experiment is to keep the proof of concepts affordable. The first time you ask for $80k for something that quickly turns into shelfware will be the last time you are given a check for $80k.

Start small and build. It is much easier to make the case for resources – financial, technical and human – once your leadership team has tangible proof that your customers are finding value in your corporate blogging efforts than it is when it is all just a theoretical experiment.

But $80k is an employee’s salary for a year, so don’t be reckless about spending it. The last thing you can afford to do is to spend money foolishly only to have your efforts wither on the vine. If that happens, you can be sure the next time you need funds for another social media effort, you’re going to have a much harder fight on your hands.

One of the beauties in Web 2.0 is that affordable solutions can be found everywhere. And no, they may not have all the bells and whistles you are looking for, but an organization that is dipping its collective toes in the water needs to start somewhere. You have to walk before you can run. Once you’re up to speed, then that fancy platform might make sense, but until you know for sure, don’t burn bridges by unnecessarily burning through money.

I’m a big fan of the value of blogs as a customer service tool. But remember, your marketing people are not your customer service people. What people look for in social media is authenticity – they know it when they see it and they know when someone is faking it. So don’t try to have a marketing team pretend to speak for all of the other departments in an organization. Get the other teams involved, and let Marketing direct the efforts (or be the “project manager,” as it were). Not only will you get better results, but you’ll also be far less likely to burn out your writers and bore your readers.

Cross-posted at Social Computing Magazine.

While I find nothing inherently surprising in that statistic, I do find the reasoning behind it fundamentally flawed: the reason that supervisors “don’t have time” is because they have not made it a priority.

In reviewing the results of the survey, each of the different categories of answers warrants some consideration. In response to the question, “What is the biggest challenge you face in coaching others?” the answers breakdown as follows:

“It takes too long.”
This is a response I find bothersome and a bit lazy. As a manager, your success is directly dependent on the success of your direct reports. If ‘it takes too long’ to coach someone, then that says one of two things to me: either you aren’t doing it well and need some guidance on technique, or you are looking at it as a disparate task instead of an integrated part of your daily job responsibilities. Either way, a manager who gives this answer is not managing their priorities very closely.

“I don’t have all the answers.”
This is the perfectionist’s answer, and it’s one that is hard to get a perfectionist not to rely on. No one has all the answers. That is not what coaching is about. Coaching is about helping and guiding someone else to finding the answers they need — whether it’s because you have them and can give them, or because you help them brainstorm on where else they can go to find them. That old saying about giving a man a fish vs. teaching him to fish is the heart of coaching. Any coach who claims to have all the answers is full of it, and any coach who tries to give someone all the answers isn’t teaching them how to find them on their own.

“I have too many direct reports.”
This one I find to be the most genuinely legitimate of the reasons given: I have seen more organizations than I can count where a person is put in charge of too many people (often along side a long list of other responsibilities that have nothing to do with people management whatsoever) and then told to manage everything on their own. Managing people does indeed take time, thoughtfulness and a sincere effort to learn about the people you are trying to coach. If you have too many direct reports then no amount of prioritizing is going to allow you to be a true coach to all of them.

“I am not sure where to start.”
Two words: Training Issue. Like anything else, getting started is often the hardest part. But the more you focus on how hard it is, the more you paralyze yourself into inaction. Before you sink into paralysis by analysis, start small by asking questions. “What do you like doing?” “What is important to you about a job?” “What do you most love/hate/fear doing as a part of your work?” “If you could make a living doing anything in the world, what would it be?” The heart of coaching well is knowing who you are coaching, and you can’t know how to help lead someone if you have no idea where they are interested in going. So start asking.

“I don’t see the results of my efforts.”
This response strikes me as a bit selfish and, honestly, irrelevant. Yes, obviously we all like (and to some degree need) to see results of our actions to stay motivated. However, if you are not seeing any results then there are two very likely causes: your efforts to date have been too inconsistent to produce results or you are trying to coach people who are not interested in being coached (which, incidentally, are frequently the people most in need of coaching — but that’s a topic for another time). You need to look at that and figure out which it is. You can’t go to the gym and lift weights once per month and expect to see results. If the problem is your consistency, then build yourself a plan that includes regular time spent on coaching activities. Put it on your calendar and build it into your schedule. If the problem is that you are trying to coach people who aren’t interested, then the question arises: are they not interested because they think they don’t need it or because they think you aren’t qualified. And after that, the next question is: are they right?

“I am not comfortable having coaching discussions.”
Again, this strikes me as a training and (ultimately) practice issue. Like anything new, coaching takes practice before you start to feel competent and confident in your ability to do it, much less do it well. But you have to start somewhere. And if you need help, then find it. There are tons of training programs designed to help train managers how to start coaching their staff.

“I don’t like to coach.”
To me this is the inexcusable answer: if you don’t like to coach, then you shouldn’t be managing people. That’s just part of the job. I once had a manager look at me and say that no one ever told him that coaching, mentoring and developing his staff was part of his job description. I was incredulous. Are you kidding me? Having a staff is like having kids: by taking on that role you are accepting responsibility for their growth and development. If you don’t want that responsibility, then don’t take that job. Period.

As I said: nothing about the results of this study surprise me, but it greatly peeves me. When I look back on the most significant coaches and mentors in my career, I see men (and, sadly, one of the downsides of being a career IT person, is that to date, all of my mentors have been men) who had far more work to get done than was ever reasonable to expect them to complete on any given day. And while they were definitely workaholics who were still responding to email at 1:00 a.m. most nights, long after their wives and children had gone to sleep, the fact was that they made coaching their staff a priority. They made the time to get to know their direct reports: what motivated them, what de-motivated them, what their strengths were, and what their Achilles Heels were. They asked questions and carefully considered the answers. They knew when to push and when to back off and let us flail a bit while we found our footing. Not one of these men were drowning in “free time.” They all had supremely (and sometimes unreasonably) demanding jobs as well as families with young children. But they took the time to coach their direct reports because they knew in their bones that it was important.

So when I see that people “don’t have time,” what I really see is managers saying, “I don’t think it’s important enough to make the time.” And that just makes me sad for their direct reports, because everyone deserves a boss who will be more than a task master.