Tuckpointing is arguably the quintessence of masonry restoration and preservation.
The primary way that masonry materials are damaged, is by water. If a mortar joint is failing, or if it was installed wrong in the first place it will allow water to penetrate and cause extensive damage. The concept of tuckpointing is very simple. It involves removing the exposed mortar from the joint, and replacing it with good mortar.
However, not all tuckpoint repairs are created equal. The scourge of the masonry world is poor tuckpointing. Sometimes people do not remove the mortar deep enough, and the tuckpoint begins to fail early. Other times people install a mortar that is much too hard for the brick or stone it is going between. Causing the mortar to expand and contract at a different rate, which results in damage. Sometimes the color does not match, sometimes they do not finish the joints well, causing water penetration, and still other times, mortar is smeared all over the face of the material, causing the end product to be unsightly. In almost every case, it is more expensive and time consuming to repair poor tuckpointing, than to repair the original failed joints.
Because of this it is very important to be sure a contractor knows what they are doing before you hire them.
Here are a few things to ask potential contractors.
Ask what type of mortar they plan to use. Some will respond with a letter. Such as type N or type S, others will tell you about the mix they use. What type of mortar should be used depends on a number of factors, but it is a warning sign if they do not have an answer, or just say "normal mortar"
Ask how deep they will grind. It is cheaper and faster to only remove a little bit of mortar. But the tuckpoint will always fail if it is not ground deep enough. They should tell you that they will grind at least half an inch, if not three quarters of an inch. A rule of thumb is that you must grind double the depth, as the height of the joint.
Make sure the contractor is licensed. In Wisconsin, contractors are not allowed to work on homes and most commercial structures unless they are licensed through the state. They are required to put their state contractor certification number on all bids and contracts. If a contractor is not certified, it is a red flag.
Ask if they will use dust collection. Contractors are required to use dust collection when they grind or drill masonry materials, but many do not. This may seem like it is only a hazard to the workers, but that is not the case. All that dust in the air is a health hazard for everybody, especially if you are in a public area. Additionally, it can damage things like screens, air conditioning units, and vehicles. Including those of your neighbors. Be wary of a contractor that does not want to use dust collection.
Ask how closely they can match the color of the mortar in the wall. Especially if you are not doing a 100% tuckpoint, you want to know how obvious the new work will be. Inquire about them putting in a sample "plug" in your project. So that you can see the color similarity.
Finally, ask to see pictures of similar tuckpointing they have done in the past. Look to see if there is a lot of mortar smeared around, see if it looks consistent.