Entering the Russian Federation as a westerner doing business can now be as risky a business as it was during the Cold War. Diplomatic relations have deteriorated so much that western travellers arriving for business or diplomacy may automatically be suspected of espionage.
Entry to Russian Federation has never been straightforward, since Bolshevik times. Russia is notorious for its complex and corrupt bureaucracy, with shifting layers of responsibility between agencies for similar tasks and with the agencies notorious fighting amongst one another and within themselves. We have chosen a British passport because British citizenship is perhaps the most challenging nationality, at the current times, to obtain the right papers to enter Russia and enjoy a trouble-free stay.
The first point to note about Russian visa applications is that the real decision-making upon whether to grant a visa, and in particular the scanning of individuals' backgrounds as part of the visa process, is not made by the Russian Embassy or Consulate to which you apply at all. They are merely rubber stamp bureaucrats for a decision making process that commences with the visa agency you use to file your visa application. All high quality Russian visa agencies - the only ones you would want to use because they know what they are doing - employ people associated with the FSB, the Russian state security service. The FSB is a much larger organisation than its British equivalents, and has both more formal and less formal structures. The visa sifting and background checks will typically be undertaken by an FSB-associated official retained by the visa agency. The more senior and reputable the FSB official associated with that agency, the more credible one's visa application may be and the easier one's entry will be at the frontier.
In Russia, money talks because the entire system is corrupt and within the visa agency's fees are bribes to almost everyone. The better visa agencies will charge in the region of US$1,000 per year for a multiple entry business visa. Although you as the visa holder will not be able to tell, the visa once issued by the Russian diplomatic mission will bear an indication of the level of FSB official who approved it or who runs the visa agency as a side business. A corporate sponsor or similar will be named discreetly in the visa materials or codes, that identifies the quality of the visa agency.
This is important at three stages. Firstly, it is important at the diplomatic mission issuing your visa. You should never go to a Russian mission in person, unless to meet a senior official upon their request. Your visa agency should send a courier; behind his back will be a bribe to the consular staff to prioritise issuance of the visa. The bigger the bribe (incorporated in your fee), the quicker the visa will be issued. Secondly, you must always remember that at Russian border crossings every official is a member of the FSB. They are powerful. They can detain you at the border for long periods while extorting bribes out of you, which is the typical Russian frontier crossing experience. If your visa contains a hidden indication that a senior FSB official has approved it, you are less likely to suffer these indignities. Thirdly, this all applies when you leave the country as well: often a sigh of relief if the paranoid bureaucracy has become too much for you. But if you don't like that sort of thing, Russia is probably not your ideal business travel destination.
Another advantage of using a senior visa agency is that if your application is to be denied, you will find out before arriving at the door of the Aeroflot aircraft, or wondering why the Embassy is taking many weeks to place a sticker in your passport. You will just be given some mysterious excuse and part or all of your fee will be retained, depending on how bad a person you are in the eyes of the Russian Federation.
When approving visas, FSB officials have a system of grading business visitors according to how much of a risk of espionage or other activities contrary to the national interests of the Russian Federation you may be perceived as presenting. It is not known exactly how this works, but it is understood that certain sorts of grading entail a greater or lesser level of potential surveillance, proportionate to the issue of whether you are perceived as a harmless fool (minimal surveillance) or someone to be respected (higher surveillance). It is not necessarily the case that friends of the Russian Federation are not subject to surveillance. They may be the subject of increased surveillance, to ensure that they remain as friendly as they appear.
Whenever possible, use Russian airports rather than land borders. Airports in the Russian Federation are mostly well organised, particularly in Moscow and St Petersburg but also elsewhere. You will no longer be asked for a bribe. Your passport and visa will be processed in a businesslike way. There used to be notorious queues at Sheremetyevo, resulting in cattle-like stampedes for empty counters; but it is understood that this has recently abated. By contrast westerners using obscure (or even major) Russian land borders are just inviting a request for a bribe. If you must use land borders, make sure you do so accompanied by savvy Russians who you trust.
Evidence of travel to and from Ukraine by a westerner makes no difference to ease of travel in and out of Russia, in the experience of the author. However travelling with a Ukrainian citizen you may be delayed by reason of the harassment the Ukrainian may suffer (depending upon gender, age and fluency in Russian).
The FSB maintains a central database of all entries to and exits from the Russian Federation by all persons worldwide, including Russians and foreigners, which is searchable by name (in any script) and date of birth. When enquiry was last made, this database also recorded internal Russian train journeys but not internal Russian air travel or hotel bookings. Nevertheless it is safe to assume that if the FSB does want to monitor where you are staying and which flights you are taking in the country, they have the means easily and costlessly to do so.
Russia is an exciting and beautiful country, of wonderfully warm-hearted and eccentric people. However its immigration system is tough, in bizarre ways you may never have thought of, and when you hit the bizarre rules it is often difficult to bribe out of them at any affordable price (although many may offer their services to do so as facilitators). Any activity contrary to the interests of the Russian Federation inside its territory is a dangerous proposition, because the extent of the FSB's intelligence gathering capacity, particularly in the information technology field, is so pervasive, and the legal system is entirely malleable to political ends if it is so decided in senior government. We recommend all business travellers to Russia to limit their activities to legitimate business. It does not matter if your business activities bring you into ceaseless conflict with your Russian counterparts; that is expected and usual in Russian business practice. But do not cross the line of infringing upon the interests of the state, or you will know about it very soon.