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Anticipating a difficult conversation? Want help? There’s plenty to be had, last week’s KJR being just one example among many. The short version: Know your goals, and plan for both the situation and how the other person is likely to respond, to the extent you’re able to anticipate it.

But how about the easy ones? The hard ones are … well, the word “harder” comes to mind … but just because they’re hard, that doesn’t make them more important.

And just because the other ones are easier, that just means they’re less hard. It doesn’t mean you should dismiss them as easy.

And even if they’re less important taken one at a time, in the aggregate they matter more.

Figure it this way: For every difficult conversation you have, you probably have 10 to 20 that aren’t hard in the usual sense. And if you’re like most of the busy managers I know, for every not-difficult conversation you have, there are probably another 10 to 20 you should have had, had you had enough time to have them.

Then figure it this way: A gram of prevention being worth easily a dekagram of cure (note to self: the metric system might be more logical than the English system, but it’s far less poetic) … where was I? That’s right, prevention, cure … handle the easier conversations and handle them well, and you won’t need as many difficult ones.

Some guidelines:

Know your goal: Are you trying to inform? Persuade? Learn? Collaboratively solve a problem? If you aren’t clear in your own mind about your goal, odds are your conversation will take too long and accomplish too little.

Know your meta-goals: When the conversation finishes, what state of mind do you want the other party to leave with? If, for example, you’re having the conversation to make you smarter about something, your meta-goal might be for the other party to feel energized because her manager values her expertise.

Schedule. Or don’t: The other person’s habits, preferences, and current time pressures, along with your goals and the complexity of the topic, all feed into your decision as to whether to IM, email, schedule a conversation, or just drop by (local) or call (remote) for a quick chat.

Choose wrong, like, for example, dropping by for a chat when the other person is crunching against a tight deadline, and what should have been an easy conversation can quickly turn difficult.

Plan: Sketch an outline for the conversation. For a group meeting this would be the agenda. Just because it’s a one-on-one that doesn’t mean you shouldn’t have a plan.

Be flexible: It’s just like any other plan — don’t insist on adhering to it if you find the conversation going in a productive direction you didn’t anticipate.

Location, location, location: The setting matters. You behind your desk in your office sets a very different tone from the two of you sitting at a table, which sets a very different tone from you in a chair facing the other person at his desk. Which in turn sets a different tone from meeting for coffee, which is different from meeting for lunch in the cafeteria or for beer after hours.

Phone calls have different dynamics entirely, and they’re different from web conferencing when there’s PowerPoint involved.

Have a meeting instead: Sometimes, when a lot of people need to hear the same message, you and they are better off all hearing it together. Also: If the message is a compliment, that’s no topic for a one-on-one conversation. Compliments should be delivered publicly.

Sequence matters: Sometimes you need to inform more than one person, or more than one group, about something of consequence. Talking to these individuals and groups in the wrong order can, in some situations, blow up in your face.

Especially groups, because once you’ve told the first group you should assume whatever you said will, within no more than a half hour, become public knowledge.

Do it: Yes, you’re busy. But ignore the easy conversations and you’ll miss opportunities, for example, to catch an employee’s deteriorating attitude when the issues are minor and easy to resolve. Instead, they’ll fester, until the situation is so bad that you now have to have a difficult conversation instead.

There are eight tasks of leadership — eight responsibilities leaders have to master. Of them, communication is the linchpin that holds the others together. It’s a multidimensional responsibility that encompasses listening, organizational listening, informing, persuading, and facilitation. There are lots of ways even the best leaders can get it wrong.

Don’t blow the easy ones.

If your career included a technical phase it’s likely that the first project you were involved with included integration as a deliverable. The last IT project you found yourself involved in probably included integration as a deliverable as well.

It would be unsurprising if they were the same project.

Regardless of the amazing coverage of your ERP or CRM, or the depth of a new point solution … wait. I need to start that sentence over: Not “regardless,” but “because of” the amazing coverage of the systems you have or are in the process of implementing, they will have data and functional overlaps. To take an easy-to-understand example, your ERP and CRM systems both manage data about your customers somewhere in the depths of their databases.

Failure to integrate them means that any time you want information about a customer, or knowledge about customers in the aggregate, the two systems will disagree.

These disagreements are gaps. Your business sponsor will either find them, or hear about them from someone else who did. And, they’ll have sufficient sophistication to know the gaps could “easily” be closed by integrating the systems. And they’ll want to know why you didn’t take this obvious step.

Let’s role-play the conversation you would have to have with the business sponsor to get yourself off the hook. You’ll need to ask the business sponsor a few questions, to help them understand the tradeoffs the team will need to make in order for the project to move forward.

Let’s rehearse a few of the points that go into this conversation, starting with:

  • Where does one system start, and where does the other one pick up the mission?

Where systems overlap, that is, which is the source of truth?  Breaking this down further, what we are really seeing are three overlaps—Overlapping Data (both systems might need a street address), Overlapping Functional Logic (both systems need to make sure that a delivery is going to a valid location) and Overlapping Business Logic (both systems are involved in order fulfillment).

To say this gets messy is an understatement.  Ideally, if you ask your CRM and ERP systems the same question about an order, you should get the same answer, in terms of payments, fulfillment stage, delivery location, billing location and customer. But depending on how your solution will synchronize them, the answer might be to let them disagree. Is this okay? Which gets to the next question:

  • If you must choose, which system needs to be “right”?

In our conversations with our colleagues, we do need to ask which system should be considered the System of Record, which systems depend on the information from this system, and when they all must agree.

  • What’s the flip side of the coin?

How often, that is, do the two systems need to re-synchronize? Near-real time? Overnight through a batch process? At month’s end as part of closing the books? This is when you give your business sponsor the bad news about synchronization: The closer we get to real time, the more complex the engineering and the higher the cost. Not to mention the higher cost. If the business sponsor wants real time or nearly so, are they willing to pay for it?

  • Every system has data that is in some way, shape, or form, “dirty.”

CRM systems, for example, are really, really good at helping you stay connected to customers. They’ll track every interaction imaginable. They are also notorious for creating an almost schizophrenic portfolio of contacts that are, in fact, the same person, but with one letter in their name different, slightly different addresses, birthdays, and so on. It is not uncommon to have 10+ entries associated with the same human being. Which of the ten should your ERP system synchronize to?

It’s a good question with no right answer. The dirty-data problem mucks up expensive marketing campaigns, recalls or RMAs … even interpersonal interactions. CRMs are likely the worst offender, but not the only one for introducing bad data to other systems.

  • Is data cleansing in your company’s future?

Without it you’ll never finish implementing the new system. With it comes expense, implementation delays, and the certainty that three years from now you’ll have to cleanse all that data all over again.

Will this conversation with your business sponsor be easy? Sure it will. Conversations about trade-offs are always fun and games, aren’t they? But especially with your business sponsor, and then recapping the results to your team, you are going to gain trust and build alignment—which might at least make later conversations easier for everyone.